Herbicidally active 4-(3-alkylsulfinylbenzoyl)pyrazoles

ABSTRACT

4-(3-Alkylsulfinylbenzoyl)pyrazoles of the formula (I) are described as herbicides. 
                         
In this formula (I), R 1  to R 4 , X and Y are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims priority to European Application No. 08009758.7 filed May 29, 2008, the entire contents of which are incorporated by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The invention relates to the technical field of the herbicides, in particular to that of the herbicides for the selective control of broad-leafed leaves and grass weeds in crops of useful plants.

2. Description of Related Art

It has already been disclosed in various publications that certain 4-benzoylpyrazoles substituted by sulfur-containing radicals in the 3-position of the phenyl ring have herbicidal properties. Thus, EP 0 352 543 and WO 97/41106 mentions benzoylpyrazoles which may be substituted at the phenyl ring inter alia by an alkylsulfinyl radical. WO 00/03993 and WO 2008/151719 disclose inter alia 3-cyclopropyl-4-(3-alkylsulfinyl benzoyl)pyrazoles.

However, the compounds known from these publications frequently do not display a sufficient herbicidal activity. It is therefore an object of the present invention to provide alternative herbicidally active compounds.

SUMMARY OF THE INVENTION

It has now been found that certain 4-benzoylpyrazoles whose phenyl ring carries an alkylsulfinyl radical in the 3-position are especially suitable as herbicides.

The present invention relates to 4-(3-alkylsulfinylbenzoyl)pyrazoles of the formula (I) or their salts

in which

-   R¹ is (C₁-C₄)-alkyl, -   R² is hydrogen or (C₁-C₄)-alkyl, -   R³ is (C₁-C₆)-alkyl, -   R⁴ is hydrogen, (C₁-C₆)-alkylsulfonyl,     (C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, or is phenylsulfonyl,     thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl or benzyl,     each of which is substituted by m identical or different radicals     from the group consisting of halogen, (C₁-C₄)-alkyl and     (C₁-C₄)-alkoxy, -   X is hydrogen, mercapto, nitro, halogen, cyano, thiocyanato,     (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,     (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl,     (C₃-C₆)-cycloalkyl, OR⁵, OCOR⁵, OSO₂R⁵, S(O)_(n)R⁵, SO₂OR⁵,     SO₂N(R⁵)₂, NR⁵SO₂R⁵, NR⁵COR⁵, (C₁-C₆)-alkyl-S(O)_(n)R⁵,     (C₁-C₆)-alkyl-OR⁵, (C₁-C₆)-alkyl-OCOR⁵, (C₁-C₆)-alkyl-OSO₂R⁵,     (C₁-C₆)-alkyl-SO₂OR⁵, (C₁-C₆)-alkyl-SO₂N(R⁵)₂ or     (C₁-C₆)-alkyl-NR⁵COR⁵; -   Y is fluorine, chlorine, bromine, iodine, nitro or the group SO₂R⁷, -   R⁵ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,     (C₃-C₆)-cycloalkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the six     last-mentioned radicals are substituted by s radicals from the group     consisting of hydroxy, mercapto, amino, cyano, nitro, thiocyanato,     OR⁶, SR⁶, N(R⁶)₂, NOR⁶, OCOR⁶, SCOR⁶, NR⁶COR⁶, CO₂R⁶, COSR⁶,     CON(R⁶)₂, (C₁-C₄)-alkyliminooxy, (C₁-C₄)-alkylcarbonyl,     (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl and (C₁-C₄)-alkylsulfonyl; -   R⁶ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, -   R⁷ is (C₁-C₄)-alkyl, -   m is 0, 1, 2, 3, 4 or 5, -   n is 0, 1 or 2, -   s is 0, 1, 2 or 3.

In formula (I) and all formulae given below, alkyl radicals which have more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

If a group is polysubstituted by radicals, this is to be understood as meaning that this group is substituted by one or more of the abovementioned radicals which are identical or different.

Owing to the center of chirality of the sulfinyl group, the compounds of the formula (I) are present as enantiomers. In addition, depending on the nature of the substituents and on how they are attached, there may be further stereoisomers, for example in the case of asymmetrically substituted carbon atoms. Stereoisomers, if not already obtained in pure form in the synthesis, can be obtained from the mixtures generated in the course of the preparation using customary separation methods, for example by chromatographic separation methods. Equally, stereoisomers can be prepared selectively using stereoselective reactions and employing optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and their mixtures which are embraced by the formula (I), but are not specifically defined.

Preference is given to compounds of the formula (I) in which

-   R¹ is methyl, ethyl, n-propyl or isopropyl, -   R² is hydrogen, methyl, ethyl, n-propyl or isopropyl, -   R³ is (C₁-C₄)-alkyl, -   R⁴ is hydrogen, (C₁-C₃)-alkylsulfonyl,     (C₁-C₂)-alkoxy-(C₁-C₄)-alkylsulfonyl, or is phenylsulfonyl,     thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl or benzyl,     each of which is substituted by m methyl groups, -   X is nitro, halogen, (C₁-C₄)-alkyl, trifluoromethyl, (C₁-C₄)-alkoxy,     methylsulfonyl, methoxymethyl, methoxymethoxymethyl,     ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl,     methoxypropoxymethyl, methylsulfonyl methyl,     methylsulfonylethoxymethyl, methoxyethylsulfonyl methyl,     methylsulfonylethylsulfonylmethyl, -   Y is fluorine, chlorine, bromine, iodine or the group SO₂R⁷, -   R⁷ is methyl, ethyl, n-propyl or isopropyl, -   m is 0, 1, 2 or 3.

Particular preference is given to compounds of the formula (I) in which

-   R¹ is methyl or ethyl, -   R² is hydrogen, methyl or ethyl, -   R³ is methyl, ethyl, n-propyl or isopropyl, -   R⁴ is hydrogen, -   X is nitro, halogen, (C₁-C₄)-alkyl, trifluoromethyl, (C₁-C₄)-alkoxy,     methylsulfonyl, methoxymethyl, methoxymethoxymethyl,     ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl,     methoxypropoxymethyl, methylsulfonyl methyl,     methylsulfonylethoxymethyl, methoxyethylsulfonyl methyl,     methylsulfonylethylsulfonylmethyl, -   Y is fluorine, chlorine, bromine, iodine or the group SO₂R⁷, -   R⁷ is methyl or ethyl.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

Unless otherwise defined, the substituents and symbols in all the formulae mentioned hereinbelow have the same meaning as described in formula (I).

Compounds according to the invention in which R⁴ is hydrogen can be prepared, for example, by the process shown in Scheme 1 and known from WO2005/122768 by reacting a benzoic acid of the formula (II) with a pyrazole of the formula (III) in the presence of a condensing agent such as N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, followed by cyanide-catalyzed rearrangement.

Compounds of the formula (I) can be prepared, for example, by the process shown in Scheme 2 and described in WO2005/122768 by reacting a compound of the formula (Ia) with compounds of the formula (IV) in which E is a nucleophilic leaving group.

Compounds according to the invention in which R⁴ is hydrogen can also be prepared, for example, by the process shown in Scheme 3 by nucleophilic aromatic substitution from compounds of the formula (V) in which L² is, for example, a fluorine or chlorine atom using a thiolate (VI) in which M is a metal cation, followed by oxidation.

Compounds of the formula (II) can be prepared, for example, by the process shown in Scheme 4 from benzoic acids of the formula (VII) by introducing the substituent X, followed by nucleophilic aromatic substitution and then oxidation. Suitable reactions for introducing the substituent X are known, for example, from J. Chem. Soc. Perkin Trans. 1 1995, p. 1265 ff, J. Heterocyclic Chem. 1999, 36, p. 1453 ff., Angew. Chem. 2005, 117, 380-398, J. Org. Chem. 2003, 68, 2030-2033 and J. Org. Chem. 1994, 59, 4042-4044.

Compounds of the formula (II) are novel and also form part of the subject matter of the present invention.

Collections of compounds of the formula (I) and/or their salts which can be synthesized in accordance with the abovementioned reactions can also be prepared in a parallelized manner, which can be effected manually or in a partly or fully automated manner. Here, it is possible for example to automate the procedure of the reaction, the work-up or the purification of the products or intermediates. In total, this is understood as meaning a procedure as described for example by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (Editor Gunther Jung), Wiley 1999, on pages 1 to 34.

A series of commercially available apparatuses can be used for the parallelized reaction procedure and work-up, for example Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA, or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Mass. 02451, USA. Chromatographic apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA, are available, inter alia, for the parallelized purification of compounds of the formula (I) and their salts or of intermediates generated in the course of the preparation.

The apparatuses listed lead to a modular procedure in which the individual passes are automated, but manual operations must be carried out between the passes. This can be circumvented by the use of partly or fully integrated automation systems, where the relevant automation modules are operated by, for example, robots. Such automation systems can be obtained for example from Caliper, Hopkinton, Mass. 01748, USA.

The performance of individual, or a plurality of, synthesis steps can be aided by the use of polymer-supported reagents/scavenger resins. The specialist literature describes a series of experimental protocols, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

Besides the methods described herein, the preparation of compounds of the formula (I) and their salts can be effected fully or in part by solid-phase-supported methods. For this purpose, individual intermediates, or all intermediates, of the synthesis or of a synthesis adapted to the relevant procedure are bound to a synthesis resin. Solid-phase-supported synthesis methods are described sufficiently in the specialist literature, for example Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis, Analysis, Screening (Editor Gunther Jung), Wiley, 1999. The use of solid-phase-supported synthesis methods permits a series of protocols known from the literature, which, again, can be carried out manually or in an automated manner. For example, the reactions can be carried out by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Carrying out individual or a plurality of synthesis steps, both on a solid and in the liquid phase, can be aided by the use of microwave technology. A series of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (Editors C. O. Kappe and A. Stadler), Wiley, 2005.

The preparation in accordance with the processes described herein generates compounds of the formula (I) and their salts in the form of substance collections, which are referred to as libraries. The present invention also relates to libraries which comprise at least two compounds of the formula (I) and their salts.

The compounds of the formula (I) according to the invention (and/or their salts), hereinbelow together referred to as “compounds according to the invention”, have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active substances also act efficiently on perennial harmful plants which produce shoots from rhizomes, rootstocks or other perennial organs and which are difficult to control.

The present invention therefore also relates to a method of controlling unwanted plants or for regulating the growth of plants, preferably in crops of plants, where one or more compound(s) according to the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), to the seeds (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or to the area on which the plants grow (for example the area under cultivation). In this context, the compounds according to the invention can be applied for example pre-planting (if appropriate also by incorporation into the soil), pre-emergence or post-emergence. Examples of individual representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention shall be mentioned, without the mention being intended as a limitation to certain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the compounds according to the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they have reached the cotyledon stage, but then stop their growth and, finally, die completely after three to four weeks have elapsed.

When the active substances are applied post-emergence to the green plant parts, growth stops after the treatment, and the harmful plants remain in the growth stage of the time of application or die fully after a certain period of time, so that competition by weeds, which is harmful to the crop plants, is thus eliminated at an early point in time and in a sustained manner.

Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. This is why the present compounds are highly suitable for the selective control of undesired plant growth in plant crops such as agriculturally useful plants or ornamentals.

Moreover, the compounds according to the invention (depending on their respective structure and the application rate applied) have outstanding growth-regulatory properties in crop plants. They engage in the plant metabolism in a regulatory fashion and can therefore be employed for the influencing, in a targeted manner, of plant constituents and for facilitating harvesting, such as, for example, by triggering desiccation and stunted growth. Moreover, they are also suitable for generally controlling and inhibiting undesired vegetative growth without destroying the plants in the process. Inhibiting the vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops since for example lodging can be reduced, or prevented completely, hereby.

Owing to their herbicidal and plant-growth-regulatory properties, the active substances can also be employed for controlling harmful plants in crops of genetically modified plants or plants which have been modified by conventional mutagenesis. As a rule, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to certain pesticides, mainly certain herbicides, resistances to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate for example to the harvested material with regard to quantity, quality, storability, composition and specific constituents. Thus, transgenic plants with an increased starch content or a modified starch quality or those with a different fatty acid composition of the harvested material are known.

It is preferred to use the compounds according to the invention or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, sorghum and millet, rice, cassaya and maize or else crops of sugar beet, cotton, soybean, oil seed rape, potato, tomato, peas and other vegetables. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

Conventional ways of generating novel plants which, in comparison with existing plants, have modified properties are, for example, traditional breeding methods and the generation of mutants. Alternatively, novel plants with modified properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following have been described in several cases:

-   -   recombinant modifications of crop plants for the purposes of         modifying the starch synthesized in the plants (for example WO         92/11376, WO 92/14827, WO 91/19806),     -   transgenic crop plants which are resistant to certain herbicides         of the glufosinate type (cf., for example, EP-A-0242236,         EP-A-242246) or of the glyphosate type (WO 92/00377) or of the         sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),     -   transgenic crop plants, for example cotton, which is capable of         producing Bacillus thuringiensis toxins (Bt toxins), which make         the plants resistant to certain pests (EP-A-0142924,         EP-A-0193259),     -   transgenic crop plants with a modified fatty acid composition         (WO 91/13972),     -   genetically modified crop plants with novel constituents or         secondary metabolites, for example novel phytoalexins, which         bring about an increased disease resistance (EPA 309862,         EPA0464461),     -   genetically modified plants with reduced photorespiration which         feature higher yields and higher stress tolerance (EPA 0305398),     -   transgenic crop plants which produce pharmaceutically or         diagnostically important proteins (“molecular pharming”),     -   transgenic crop plants which are distinguished by higher yields         or better quality,     -   transgenic crop plants which are distinguished by a combination,         for example of the abovementioned novel properties (“gene         stacking”).

A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1 (1996) 423-431).

To carry out such recombinant manipulations, it is possible to introduce nucleic acid molecules into plasmids, which permit a mutagenesis or sequence modification by recombination of DNA sequences. For example, base substitutions can be carried out, part-sequences can be removed, or natural or synthetic sequences may be added with the aid of standard methods. To link the DNA fragments with one another, it is possible to add adapters or linkers to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone”, VCH Weinheim 2nd ed., 1996

The generation of plant cells with a reduced activity for a gene product can be achieved for example by the expression of at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect or by the expression of at least one correspondingly constructed ribozyme, which specifically cleaves transcripts of the abovementioned gene product. To do this, it is possible firstly to use DNA molecules which comprise all of the coding sequence of a gene product, including any flanking sequences which may be present, or else DNA molecules which only comprise parts of the coding sequence, it being necessary for these parts to be long enough to bring about an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology with the coding sequences of a gene product, but which are not entirely identical.

When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any compartment of the plant cell. In order to achieve localization in a particular compartment, however, it is possible for example to link the coding region to DNA sequences which ensure the localization in a specific compartment. Such sequences are known to the skilled worker (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques to give intact plants. In principle, the transgenic plants may be plants of any plant species, that is to say both monocotyledonous and dicotyledonous plants.

Thus, transgenic plants can be obtained which feature modified properties as the result of overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

It is preferred to employ the compounds according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or against herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or against herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active substances.

When the active substances according to the invention are used in transgenic crops, effects are frequently observed—in addition to the effects on harmful plants which can be observed in other crops—which are specific for the application in the transgenic crop in question, for example a modified or specifically widened spectrum of weeds which can be controlled, modified application rates which may be employed for application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and an effect on growth and yield of the transgenic crop plants.

The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

The compounds according to the invention can be employed in the customary preparations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also relates to herbicidal and plant-growth-regulating compositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in various ways, depending on the prevailing biological and/or physico-chemical parameters. Examples of possible formulations are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed-dressing products, granules for application by broadcasting and on the soil, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials, surfactants, solvents and further additives, are also known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix.

Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance, also comprise ionic and/or nonionic surfactants (wetters, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate, besides a diluent or inert substance. To prepare the wettable powders, the herbicidally active substances are ground finely, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and mixed with the formulation auxiliaries, either simultaneously or subsequently.

Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan esters such as, for example, sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as, for example, polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active substance with finely divided solid materials such as, for example, talcum, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be water- or oil-based. They can be prepared for example by wet-grinding by means of commercially available bead mills, if appropriate with addition of surfactants as already listed above for example in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if appropriate, surfactants, as have already been mentioned for example above for the other formulation types.

Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material, or by applying active substance concentrates to the surface of carriers such as sand, kaolinites or granulated inert material with the aid of stickers, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances can also be granulated in the manner which is customary for the production of fertilizer granules, if desired as a mixture with fertilizers.

Water-dispersible granules are generally prepared by customary methods such as spray drying, fluidized-bed granulation, disk granulation, mixing with high-speed stirrers, and extrusion without solid inert material.

To prepare disk granules, fluidized-bed granules, extruder granules and spray granules, see, for example, methods in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 et seq.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, p. 8-57.

For further details of the formulation of crop protection products see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

As a rule, the agrochemical preparations comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active substance concentration is, for example, approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation constituents. In the case of emulsifiable concentrates, the active substance concentration can amount to approximately 1 to 90, preferably 5 to 80% by weight. Formulations in the form of dusts comprise from 1 to 30% by weight of active substance, preferably in most cases from 5 to 20% by weight of active substance, and sprayable solutions comprise approximately from 0.05 to 80, preferably from 2 to 50% by weight of active substance. In the case of water-dispersible granules, the active substance content depends partly on whether the active compound is in liquid or solid form, and on the granulation auxiliaries, fillers and the like which are being used. In the case of the water-dispersible granules, for example, the active substance content is between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active substance formulations mentioned comprise, if appropriate, the auxiliaries which are conventional in each case, such as stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors, and pH and viscosity regulators.

Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix.

Active substances which can be employed in combination with the compounds according to the invention in mixed formulations or in the tank mix are, for example, known active substances which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active substances (the compounds are either designated by the common name according to the International Organization for Standardization (ISO) or by a chemical name, if appropriate together with the code number) and always comprise all use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. In this context, one and in some cases also several use forms are mentioned by way of example:

acetochlor, acibenzolar, acibenzolar-5-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryne, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryne, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, BAS-800H, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, L-glufosinate, L-glufosinate-ammonium, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, H-9201, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HNPC-9908, HOK-201, HW-02, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, inabenfide, indanofan, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, KUH-071, karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat-chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, methazole, methoxyphenone, methyldymron, 1-methylcyclopropene, methyl isothiocyanate, metobenzuron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrogen sulfate, monolinuron, monosulfuron, monuron, MT 128, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolat-sodium (isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazol, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyzamide, prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, sulcotrione, sulf-allate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249, SYP-298, SYP-300, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryne, TH-547, thenylchlor, thiafluamide, thiazafluoron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0166, ZJ-0270, ZJ-0543, ZJ-0862 and the following compounds

For use, the formulations, which are present in commercially available form, if appropriate, are diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, soil granules, granules for broadcasting, and sprayable solutions, are usually not diluted further with further inert substances prior to use.

The application rate required of the compounds of the formula (I) varies as a function of the external conditions such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha and more of active substance, but it is preferably between 0.005 and 750 g/ha.

The examples which follow are intended to illustrate the invention.

A. CHEMICAL EXAMPLES 1. Preparation of 4-(4-chloro-3-ethylsulfinyl-2-methyl benzoyl)-5-hydroxy-1,3-dimethylpyrazole (No. 3-238 of Table 3) Step 1: Synthesis of methyl 4-chloro-3-(dimethylaminothiocarbonyloxy)-2-methylbenzoate

Under an atmosphere of nitrogen, 12.3 g (109.7 mmol) of 1,4-diazabicyclo[2.2.2]octane and then 13.6 g (109.7 mmol) of dimethylaminothiocarbonyl chloride were added to 11.0 g (54.8 mmol) of methyl 4-chloro-3-hydroxy-2-methylbenzoate in 200 ml of N,N-dimethylformamide. The mixture was stirred at room temperature (RT) for 16 h and, for work-up, poured on ice-water. The product precipitated out and was removed by filtration. The residue was washed with 1M HCl. This gave 14.7 g of clean product.

Step 2: Synthesis of methyl 4-chloro-3-(dimethylaminocarbonylthio)-2-methylbenzoate

Under an atmosphere of nitrogen, 12.1 g (42.0 mmol) of methyl 4-chloro-3-(dimethylaminothiocarbonyloxy)-2-methylbenzoate in 30 ml of 1,3-dimethoxybenzene were heated at 220° C. for 6 h. For work-up, the reaction mixture was cooled and concentrated under reduced pressure. After chromatographic purification of the residue, 5.2 g of clean product were isolated.

Step 3: Synthesis of 4-chloro-3-mercapto-2-methylbenzoic acid

6.61 g (85% by weight pure, 100.1 mmol) of potassium hydroxide were added to 4.80 g (16.7 mmol) of methyl 4-chloro-3-(dimethylaminocarbonylthio)-2-methylbenzoate in 150 ml of methanol, and the mixture was stirred under reflux for two days. The reaction mixture was freed from the solvent, water was added to the residue, the mixture was acidified with 1M HCl and the solid was removed by filtration. This gave 3.2 g of clean product.

Step 4: Synthesis of 4-chloro-3-ethylthio-2-methylbenzoic acid

3.71 g (11.3 mmol) of cesium carbonate were added to 1.10 g (5.42 mmol) of 4-chloro-3-mercapto-2-methylbenzoic acid in 20 ml of acetonitrile. The reaction mixture was stirred at RT for 10 min, and 1.02 g (6.51 mmol) of iodoethane were then slowly added dropwise. The reaction mixture was then stirred at RT for 16 h. The solvent was then removed, and a mixture of 20 ml of methanol and 2 ml of 20% strength aqueous sodium hydroxide solution was then added to the reaction mixture. For the hydrolysis of the ethyl ester formed, the mixture was stirred at RT for 16 h and then freed from the solvents. The residue was taken up in water and acidified with diluted HCl, and the mixture was stirred at RT for 10 min and then filtered. The residue was washed with water and sucked dry. 1.15 g of clean product were isolated.

Step 5: Synthesis of 4-chloro-3-ethylsulfinyl-2-methylbenzoic acid (No. 4-238)

1.15 g (4.98 mmol) of 4-chloro-3-ethylthio-2-methylbenzoic acid in 10 ml of glacial acetic acid were heated to a temperature of 50° C.-60° C. At this temperature, 484 mg (35% strength, 4.98 mmol) of an aqueous hydrogen peroxide solution were added dropwise. The mixture was stirred at this temperature for 5 h. The reaction mixture was cooled, washed with an aqueous saturated sodium bisulfite solution and, after analytical proof of absence of peroxides, freed from the solvents. Water was added to the residue, and the mixture was acidified with 6M HCl. The mixture was extracted with ethyl acetate, and the combined organic phases were dried, filtered and, under reduced pressure, freed from the solvent. 1.24 g of the product (purify about 95% by weight) were isolated.

Step 6: Synthesis of 4-(4-chloro-3-ethylsulfinyl-2-methyl benzoyl)-5-hydroxy-1,3-dimethylpyrazole

128 mg (1.14 mmol) of 5-hydroxy-1,3-dimethylpyrazole were added to 270 mg (purity 95% by weight; 1.04 mmol) of 4-chloro-3-ethylsulfinyl-2-methylbenzoic acid in 20 ml of dichloromethane (CH₂Cl₂). 239 mg (1.24 mmol) of 1-(3′-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added, and the mixture was stirred at RT for 16 h. For work-up, 3 ml of 1M HCl were added, and the organic phase was freed from the solvent. 210 mg (2.07 mmol) of triethylamine, 10 drops of acetone cyanohydrin and a spatula tip of potassium cyanide were added to the residue in 20 ml of acetonitrile. The reaction mixture was stirred at RT for 16 h and then freed from the solvent. The residue was stirred at RT with 25 ml of a mixture of aqueous saturated sodium bicarbonate solution and diethyl ether for 10 min. The phases were separated, and the aqueous phase was acidified with dilute HCl and then extracted with CH₂Cl₂. The organic phase was freed from the solvent and the residue was then purified chromatographically. This gave 100 mg of clean product.

2. Preparation of 5-hydroxy-1-methyl-4-(2-methyl-3-methylsulfinyl-4-methylsulfonylbenzoyl)pyrazole (No. 1-9 of Table 1) Step 1: Synthesis of 2-methyl-3-methylsulfinyl-4-methylsulfonylbenzoic acid (No. 4-9)

900 mg (3.45 mmol) of 2-methyl-4-methylsulfonyl-3-methylthiobenzoic acid in 10 ml of glacial acetic acid were heated to a temperature of 50° C.-60° C. At this temperature, 336 mg (35% strength, 3.45 mmol) of an aqueous hydrogen peroxide solution were added dropwise. The mixture was stirred at 60° C. for 5 h. The reaction mixture was cooled, washed with an aqueous 10% strength sodium bisulfite solution and, after analytical proof of absence of peroxides, freed from the solvents. Water was added to the residue, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried, filtered and, under reduced pressure, freed from the solvent. 950 mg of the clean product were isolated.

Step 2: Synthesis of 5-hydroxy-1-methyl-4-(2-methyl-3-methylsulfinyl-4-methylsulfonylbenzoyl)pyrazole

90 mg (0.91 mmol) of 5-hydroxy-1-methylpyrazole and a spatula tip of 4-(dimethylamino)pyridine were added to 230 mg (0.83 mmol) of 2-methyl-3-methylsulfinyl-4-methylsulfonylbenzoic acid in 20 ml of CH₂Cl₂. 191 mg (0.99 mmol) of 1-(3′-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added, and the mixture was stirred at RT for 90 min. 3 ml of 1M HCl were then added, and the organic phase was freed from the solvent. 168 mg (1.66 mmol) of triethylamine, 10 drops of acetone cyanohydrin and a spatula tip of potassium cyanide were added to the residue in 15 ml of acetonitrile. The reaction mixture was stirred at RT for 16 h and then freed from the solvent. 15 ml of CH₂Cl₂ were added to the residue, and 2 ml of 1M HCl were then added. After phase separation, the organic phase was freed from the solvent. The residue was stirred with 25 ml of a mixture of aqueous saturated sodium bicarbonate solution and diethyl ether at RT for 10 min. The phases were separated, and the aqueous phase was acidified with dilute HCl and then extracted three times with CH₂Cl₂. The combined organic phases were freed from the solvent. This gave 171 mg of clean product.

The examples listed in the tables hereinbelow were prepared analogously to abovementioned methods or are obtainable analogously to above-mentioned methods. These compounds are very particularly preferred.

TABLE 1 Compounds of the formula (I) according to the invention in which R¹ is methyl, R² and R⁴ are each hydrogen.

Physical data: No. X R³ Y ¹H—NMR: δ [CDCl₃] 1-1 Cl Me SO₂Me 1-2 Cl Et SO₂Me 8.23 (d, 1 H), 7.66 (d, 1 H), 7.32 (s, 1 H), 3.92 (m, 1 H), 3.73 (s, 3 H), 3.45 (s, 3 H), 3.28 (m, 1 H), 1.53 (t, 3 H) 1-3 Cl n-Pr SO₂Me 1-4 Cl i-Pr SO₂Me 1-5 Br Me SO₂Me 1-6 Br Et SO₂Me 1-7 Br n-Pr SO₂Me 1-8 Br i-Pr SO₂Me 1-9 Me Me SO₂Me 8.08 (d, 1 H), 7.62 (d, 1 H), 7.27 (s, 1 H), 3.72 (s, 3 H), 3.38 (s, 3 H), 3.18 (s, 3 H), 2.87 (s, 3 H) 1-10 Me Et SO₂Me 8.08 (d, 1 H), 7.61 (d, 1 H), 7.27 (s, 1 H), 3.72 (s, 3 H), 3.52 (m, 1 H), 3.38 (s, 3 H), 3.28 (m, 1 H), 2.82 (s, 3 H), 1.52 (t, 3 H) 1-11 Me n-Pr SO₂Me 1-12 Me i-Pr SO₂Me 1-13 Et Me SO₂Me 1-14 Et Et SO₂Me 1-15 Et n-Pr SO₂Me 1-16 Et i-Pr SO₂Me 1-17 CF₃ Me SO₂Me 1-18 CF₃ Et SO₂Me 1-19 CF₃ n-Pr SO₂Me 1-20 CF₃ i-Pr SO₂Me 1-21 OMe Me SO₂Me 1-22 OMe Et SO₂Me 1-23 OMe n-Pr SO₂Me 1-24 OMe i-Pr SO₂Me 1-25 OEt Me SO₂Me 1-26 OEt Et SO₂Me 1-27 OEt n-Pr SO₂Me 1-28 OEt i-Pr SO₂Me 1-29 NO₂ Me SO₂Me 1-30 NO₂ Et SO₂Me 1-31 NO₂ n-Pr SO₂Me 1-32 NO₂ i-Pr SO₂Me 1-33 SO₂Me Me SO₂Me 1-34 SO₂Me Et SO₂Me 1-35 SO₂Me n-Pr SO₂Me 1-36 SO₂Me i-Pr SO₂Me 1-37 CH₂OMe Me SO₂Me 1-38 CH₂OMe Et SO₂Me 1-39 CH₂OMe n-Pr SO₂Me 1-40 CH₂OMe i-Pr SO₂Me 1-41 CH₂SO₂Me Me SO₂Me 1-42 CH₂SO₂Me Et SO₂Me 1-43 CH₂SO₂Me n-Pr SO₂Me 1-44 CH₂SO₂Me i-Pr SO₂Me 1-45 CH₂OCH₂CH₂OMe Me SO₂Me 8.21 (d, 1 H), 7.67 (d, 1 H), 7.37 (s, 1 H), 5.57-5.32 (br. signal, 1 H), 5.00 (d, 1 H), 3.72 (s, 3 H), 3.63-3.58 (m, 1 H), 3.56-3.50 (m, 1 H), 3.42-3.25 (m, 2 H), 3.37 (s, 3 H), 3.32 (s, 3 H), 3.23 (s, 3 H) 1-46 CH₂OCH₂CH₂OMe Et SO₂Me 1-47 CH₂OCH₂CH₂OMe n-Pr SO₂Me 1-48 CH₂OCH₂CH₂OMe i-Pr SO₂Me 1-49 CH₂OCH₂CH₂OEt Me SO₂Me 1-50 CH₂OCH₂CH₂OEt Et SO₂Me 1-51 CH₂OCH₂CH₂OEt n-Pr SO₂Me 1-52 CH₂OCH₂CH₂OEt i-Pr SO₂Me 1-53 CH₂OCH₂CH₂CH₂OMe Me SO₂Me 1-54 CH₂OCH₂CH₂CH₂OMe Et SO₂Me 1-55 CH₂OCH₂CH₂CH₂OMe n-Pr SO₂Me 1-56 CH₂OCH₂CH₂CH₂OMe i-Pr SO₂Me 1-57 CH₂OCH₂OMe Me SO₂Me 1-58 CH₂OCH₂OMe Et SO₂Me 1-59 CH₂OCH₂OMe n-Pr SO₂Me 1-60 CH₂OCH₂OMe i-Pr SO₂Me 1-61 CH₂OCH₂OEt Me SO₂Me 1-62 CH₂OCH₂OEt Et SO₂Me 1-63 CH₂OCH₂OEt n-Pr SO₂Me 1-64 CH₂OCH₂OEt i-Pr SO₂Me 1-65 CH₂OCH₂CH₂SO₂Me Me SO₂Me 1-66 CH₂OCH₂CH₂SO₂Me Et SO₂Me 1-67 CH₂OCH₂CH₂SO₂Me n-Pr SO₂Me 1-68 CH₂OCH₂CH₂SO₂Me i-Pr SO₂Me 1-69 CH₂SO₂CH₂CH₂OMe Me SO₂Me 1-70 CH₂SO₂CH₂CH₂OMe Et SO₂Me 1-71 CH₂SO₂CH₂CH₂OMe n-Pr SO₂Me 1-72 CH₂SO₂CH₂CH₂OMe i-Pr SO₂Me 1-73 CH₂SO₂CH₂CH₂SO₂Me Me SO₂Me 1-74 CH₂SO₂CH₂CH₂SO₂Me Et SO₂Me 1-75 CH₂SO₂CH₂CH₂SO₂Me n-Pr SO₂Me 1-76 CH₂SO₂CH₂CH₂SO₂Me i-Pr SO₂Me 1-77 Cl Me SO₂Et 1-78 Cl Et SO₂Et 1-79 Cl n-Pr SO₂Et 1-80 Cl i-Pr SO₂Et 1-81 Br Me SO₂Et 1-82 Br Et SO₂Et 1-83 Br n-Pr SO₂Et 1-84 Br i-Pr SO₂Et 1-85 Me Me SO₂Et 1-86 Me Et SO₂Et 1-87 Me n-Pr SO₂Et 1-88 Me i-Pr SO₂Et 1-89 Et Me SO₂Et 1-90 Et Et SO₂Et 1-91 Et n-Pr SO₂Et 1-92 Et i-Pr SO₂Et 1-93 CF₃ Me SO₂Et 1-94 CF₃ Et SO₂Et 1-95 CF₃ n-Pr SO₂Et 1-96 CF₃ i-Pr SO₂Et 1-97 OMe Me SO₂Et 1-98 OMe Et SO₂Et 1-99 OMe n-Pr SO₂Et 1-100 OMe i-Pr SO₂Et 1-101 OEt Me SO₂Et 1-102 OEt Et SO₂Et 1-103 OEt n-Pr SO₂Et 1-104 OEt i-Pr SO₂Et 1-105 NO₂ Me SO₂Et 1-106 NO₂ Et SO₂Et 1-107 NO₂ n-Pr SO₂Et 1-108 NO₂ i-Pr SO₂Et 1-109 SO₂Me Me SO₂Et 1-110 SO₂Me Et SO₂Et 1-111 SO₂Me n-Pr SO₂Et 1-112 SO₂Me i-Pr SO₂Et 1-113 CH₂OMe Me SO₂Et 1-114 CH₂OMe Et SO₂Et 1-115 CH₂OMe n-Pr SO₂Et 1-116 CH₂OMe i-Pr SO₂Et 1-117 CH₂SO₂Me Me SO₂Et 1-118 CH₂SO₂Me Et SO₂Et 1-119 CH₂SO₂Me n-Pr SO₂Et 1-120 CH₂SO₂Me i-Pr SO₂Et 1-121 CH₂OCH₂CH₂OMe Me SO₂Et 1-122 CH₂OCH₂CH₂OMe Et SO₂Et 1-123 CH₂OCH₂CH₂OMe n-Pr SO₂Et 1-124 CH₂OCH₂CH₂OMe i-Pr SO₂Et 1-125 CH₂OCH₂CH₂OEt Me SO₂Et 1-126 CH₂OCH₂CH₂OEt Et SO₂Et 1-127 CH₂OCH₂CH₂OEt n-Pr SO₂Et 1-128 CH₂OCH₂CH₂OEt i-Pr SO₂Et 1-129 CH₂OCH₂CH₂CH₂OMe Me SO₂Et 1-130 CH₂OCH₂CH₂CH₂OMe Et SO₂Et 1-131 CH₂OCH₂CH₂CH₂OMe n-Pr SO₂Et 1-132 CH₂OCH₂CH₂CH₂OMe i-Pr SO₂Et 1-133 CH₂OCH₂OMe Me SO₂Et 1-134 CH₂OCH₂OMe Et SO₂Et 1-135 CH₂OCH₂OMe n-Pr SO₂Et 1-136 CH₂OCH₂OMe i-Pr SO₂Et 1-137 CH₂OCH₂OEt Me SO₂Et 1-138 CH₂OCH₂OEt Et SO₂Et 1-139 CH₂OCH₂OEt n-Pr SO₂Et 1-140 CH₂OCH₂OEt i-Pr SO₂Et 1-141 CH₂OCH₂CH₂SO₂Me Me SO₂Et 1-142 CH₂OCH₂CH₂SO₂Me Et SO₂Et 1-143 CH₂OCH₂CH₂SO₂Me n-Pr SO₂Et 1-144 CH₂OCH₂CH₂SO₂Me i-Pr SO₂Et 1-145 CH₂SO₂CH₂CH₂OMe Me SO₂Et 1-146 CH₂SO₂CH₂CH₂OMe Et SO₂Et 1-147 CH₂SO₂CH₂CH₂OMe n-Pr SO₂Et 1-148 CH₂SO₂CH₂CH₂OMe i-Pr SO₂Et 1-149 CH₂SO₂CH₂CH₂SO₂Me Me SO₂Et 1-150 CH₂SO₂CH₂CH₂SO₂Me Et SO₂Et 1-151 CH₂SO₂CH₂CH₂SO₂Me n-Pr SO₂Et 1-152 CH₂SO₂CH₂CH₂SO₂Me i-Pr SO₂Et 1-153 Cl Me F 1-154 Cl Et F 1-155 Cl n-Pr F 1-156 Cl i-Pr F 1-157 Br Me F 1-158 Br Et F 1-159 Br n-Pr F 1-160 Br i-Pr F 1-161 Me Me F 1-162 Me Et F 1-163 Me n-Pr F 1-164 Me i-Pr F 1-165 Et Me F 1-166 Et Et F 1-167 Et n-Pr F 1-168 Et i-Pr F 1-169 CF₃ Me F 1-170 CF₃ Et F 1-171 CF₃ n-Pr F 1-172 CF₃ i-Pr F 1-173 OMe Me F 1-174 OMe Et F 1-175 OMe n-Pr F 1-176 OMe i-Pr F 1-177 OEt Me F 1-178 OEt Et F 1-179 OEt n-Pr F 1-180 OEt i-Pr F 1-181 NO₂ Me F 1-182 NO₂ Et F 1-183 NO₂ n-Pr F 1-184 NO₂ i-Pr F 1-185 SO₂Me Me F 1-186 SO₂Me Et F 1-187 SO₂Me n-Pr F 1-188 SO₂Me i-Pr F 1-189 CH₂OMe Me F 1-190 CH₂OMe Et F 1-191 CH₂OMe n-Pr F 1-192 CH₂OMe i-Pr F 1-193 CH₂SO₂Me Me F 1-194 CH₂SO₂Me Et F 1-195 CH₂SO₂Me n-Pr F 1-196 CH₂SO₂Me i-Pr F 1-197 CH₂OCH₂CH₂OMe Me F 1-198 CH₂OCH₂CH₂OMe Et F 1-199 CH₂OCH₂CH₂OMe n-Pr F 1-200 CH₂OCH₂CH₂OMe i-Pr F 1-201 CH₂OCH₂CH₂OEt Me F 1-202 CH₂OCH₂CH₂OEt Et F 1-203 CH₂OCH₂CH₂OEt n-Pr F 1-204 CH₂OCH₂CH₂OEt i-Pr F 1-205 CH₂OCH₂CH₂CH₂OMe Me F 1-206 CH₂OCH₂CH₂CH₂OMe Et F 1-207 CH₂OCH₂CH₂CH₂OMe n-Pr F 1-208 CH₂OCH₂CH₂CH₂OMe i-Pr F 1-209 CH₂OCH₂OMe Me F 1-210 CH₂OCH₂OMe Et F 1-211 CH₂OCH₂OMe n-Pr F 1-212 CH₂OCH₂OMe i-Pr F 1-213 CH₂OCH₂OEt Me F 1-214 CH₂OCH₂OEt Et F 1-215 CH₂OCH₂OEt n-Pr F 1-216 CH₂OCH₂OEt i-Pr F 1-217 CH₂OCH₂CH₂SO₂Me Me F 1-218 CH₂OCH₂CH₂SO₂Me Et F 1-219 CH₂OCH₂CH₂SO₂Me n-Pr F 1-220 CH₂OCH₂CH₂SO₂Me i-Pr F 1-221 CH₂SO₂CH₂CH₂OMe Me F 1-222 CH₂SO₂CH₂CH₂OMe Et F 1-223 CH₂SO₂CH₂CH₂OMe n-Pr F 1-224 CH₂SO₂CH₂CH₂OMe i-Pr F 1-225 CH₂SO₂CH₂CH₂SO₂Me Me F 1-226 CH₂SO₂CH₂CH₂SO₂Me Et F 1-227 CH₂SO₂CH₂CH₂SO₂Me n-Pr F 1-228 CH₂SO₂CH₂CH₂SO₂Me i-Pr F 1-229 Cl Me Cl 1-230 Cl Et Cl 1-231 Cl n-Pr Cl 1-232 Cl i-Pr Cl 1-233 Br Me Cl 1-234 Br Et Cl 1-235 Br n-Pr Cl 1-236 Br i-Pr Cl 1-237 Me Me Cl 7.41 (d, 1 H), 7.36 (d, 1 H), 7.32 (s, 1 H), 3.71 (s, 3 H), 3.02 (s, 3 H), 2.74 (s, 3 H) 1-238 Me Et Cl 7.41 (d, 1 H), 7.36 (d, 1 H), 7.31 (s, 1 H), 3.71 (s, 3 H), 3.38 (m, 1 H), 3.16 (m, 1 H), 2.72 (s, 3 H), 1.41 (t, 3 H) 1-239 Me n-Pr Cl 1-240 Me i-Pr Cl 1-241 Et Me Cl 1-242 Et Et Cl 1-243 Et n-Pr Cl 1-244 Et i-Pr Cl 1-245 CF₃ Me Cl 1-246 CF₃ Et Cl 1-247 CF₃ n-Pr Cl 1-248 CF₃ i-Pr Cl 1-249 OMe Me Cl 1-250 OMe Et Cl 1-251 OMe n-Pr Cl 1-252 OMe i-Pr Cl 1-253 OEt Me Cl 1-254 OEt Et Cl 1-255 OEt n-Pr Cl 1-256 OEt i-Pr Cl 1-257 NO₂ Me Cl 1-258 NO₂ Et Cl 1-259 NO₂ n-Pr Cl 1-260 NO₂ i-Pr Cl 1-261 SO₂Me Me Cl 1-262 SO₂Me Et Cl 1-263 SO₂Me n-Pr Cl 1-264 SO₂Me i-Pr Cl 1-265 CH₂OMe Me Cl 1-266 CH₂OMe Et Cl 1-267 CH₂OMe n-Pr Cl 1-268 CH₂OMe i-Pr Cl 1-269 CH₂SO₂Me Me Cl 1-270 CH₂SO₂Me Et Cl 1-271 CH₂SO₂Me n-Pr Cl 1-272 CH₂SO₂Me i-Pr Cl 1-273 CH₂OCH₂CH₂OMe Me Cl 1-274 CH₂OCH₂CH₂OMe Et Cl 1-275 CH₂OCH₂CH₂OMe n-Pr Cl 1-276 CH₂OCH₂CH₂OMe i-Pr Cl 1-277 CH₂OCH₂CH₂OEt Me Cl 1-278 CH₂OCH₂CH₂OEt Et Cl 1-279 CH₂OCH₂CH₂OEt n-Pr Cl 1-280 CH₂OCH₂CH₂OEt i-Pr Cl 1-281 CH₂OCH₂CH₂CH₂OMe Me Cl 1-282 CH₂OCH₂CH₂CH₂OMe Et Cl 1-283 CH₂OCH₂CH₂CH₂OMe n-Pr Cl 1-284 CH₂OCH₂CH₂CH₂OMe i-Pr Cl 1-285 CH₂OCH₂OMe Me Cl 1-286 CH₂OCH₂OMe Et Cl 1-287 CH₂OCH₂OMe n-Pr Cl 1-288 CH₂OCH₂OMe i-Pr Cl 1-289 CH₂OCH₂OEt Me Cl 1-290 CH₂OCH₂OEt Et Cl 1-291 CH₂OCH₂OEt n-Pr Cl 1-292 CH₂OCH₂OEt i-Pr Cl 1-293 CH₂OCH₂CH₂SO₂Me Me Cl 1-294 CH₂OCH₂CH₂SO₂Me Et Cl 1-295 CH₂OCH₂CH₂SO₂Me n-Pr Cl 1-296 CH₂OCH₂CH₂SO₂Me i-Pr Cl 1-297 CH₂SO₂CH₂CH₂OMe Me Cl 1-298 CH₂SO₂CH₂CH₂OMe Et Cl 1-299 CH₂SO₂CH₂CH₂OMe n-Pr Cl 1-300 CH₂SO₂CH₂CH₂OMe i-Pr Cl 1-301 CH₂SO₂CH₂CH₂SO₂Me Me Cl 1-302 CH₂SO₂CH₂CH₂SO₂Me Et Cl 1-303 CH₂SO₂CH₂CH₂SO₂Me n-Pr Cl 1-304 CH₂SO₂CH₂CH₂SO₂Me i-Pr Cl 1-305 Cl Me Br 1-306 Cl Et Br 1-307 Cl n-Pr Br 1-308 Cl i-Pr Br 1-309 Br Me Br 1-310 Br Et Br 1-311 Br n-Pr Br 1-312 Br i-Pr Br 1-313 Me Me Br 7.55 (d, 1 H), 7.32 (s, 1 H), 7.30 (d, 1 H), 3.72 (s, 3 H), 3.01 (s, 3 H), 2.77 (s, 3 H) 1-314 Me Et Br 1-315 Me n-Pr Br 1-316 Me i-Pr Br 1-317 Et Me Br 1-318 Et Et Br 1-319 Et n-Pr Br 1-320 Et i-Pr Br 1-321 CF₃ Me Br 1-322 CF₃ Et Br 1-323 CF₃ n-Pr Br 1-324 CF₃ i-Pr Br 1-325 OMe Me Br 1-326 OMe Et Br 1-327 OMe n-Pr Br 1-328 OMe i-Pr Br 1-329 OEt Me Br 1-330 OEt Et Br 1-331 OEt n-Pr Br 1-332 OEt i-Pr Br 1-333 NO₂ Me Br 1-334 NO₂ Et Br 1-335 NO₂ n-Pr Br 1-336 NO₂ i-Pr Br 1-337 SO₂Me Me Br 1-338 SO₂Me Et Br 1-339 SO₂Me n-Pr Br 1-340 SO₂Me i-Pr Br 1-341 CH₂OMe Me Br 1-342 CH₂OMe Et Br 1-343 CH₂OMe n-Pr Br 1-344 CH₂OMe i-Pr Br 1-345 CH₂SO₂Me Me Br 1-346 CH₂SO₂Me Et Br 1-347 CH₂SO₂Me n-Pr Br 1-348 CH₂SO₂Me i-Pr Br 1-349 CH₂OCH₂CH₂OMe Me Br 1-350 CH₂OCH₂CH₂OMe Et Br 1-351 CH₂OCH₂CH₂OMe n-Pr Br 1-352 CH₂OCH₂CH₂OMe i-Pr Br 1-353 CH₂OCH₂CH₂OEt Me Br 1-354 CH₂OCH₂CH₂OEt Et Br 1-355 CH₂OCH₂CH₂OEt n-Pr Br 1-356 CH₂OCH₂CH₂OEt i-Pr Br 1-357 CH₂OCH₂CH₂CH₂OMe Me Br 1-358 CH₂OCH₂CH₂CH₂OMe Et Br 1-359 CH₂OCH₂CH₂CH₂OMe n-Pr Br 1-360 CH₂OCH₂CH₂CH₂OMe i-Pr Br 1-361 CH₂OCH₂OMe Me Br 1-362 CH₂OCH₂OMe Et Br 1-363 CH₂OCH₂OMe n-Pr Br 1-364 CH₂OCH₂OMe i-Pr Br 1-365 CH₂OCH₂OEt Me Br 1-366 CH₂OCH₂OEt Et Br 1-367 CH₂OCH₂OEt n-Pr Br 1-368 CH₂OCH₂OEt i-Pr Br 1-369 CH₂OCH₂CH₂SO₂Me Me Br 1-370 CH₂OCH₂CH₂SO₂Me Et Br 1-371 CH₂OCH₂CH₂SO₂Me n-Pr Br 1-372 CH₂OCH₂CH₂SO₂Me i-Pr Br 1-373 CH₂SO₂CH₂CH₂OMe Me Br 1-374 CH₂SO₂CH₂CH₂OMe Et Br 1-375 CH₂SO₂CH₂CH₂OMe n-Pr Br 1-376 CH₂SO₂CH₂CH₂OMe i-Pr Br 1-377 CH₂SO₂CH₂CH₂SO₂Me Me Br 1-378 CH₂SO₂CH₂CH₂SO₂Me Et Br 1-379 CH₂SO₂CH₂CH₂SO₂Me n-Pr Br 1-380 CH₂SO₂CH₂CH₂SO₂Me i-Pr Br 1-381 Cl Me I 1-382 Cl Et I 1-383 Cl n-Pr I 1-384 Cl i-Pr I 1-385 Br Me I 1-386 Br Et I 1-387 Br n-Pr I 1-388 Br i-Pr I 1-389 Me Me I 7.86 (d, 1 H), 7.31 (s, 1 H), 7.11 (d, 1 H), 3.71 (s, 3 H), 2.98 (s, 3 H), 2.76 (s, 3 H) 1-390 Me Et I 1-391 Me n-Pr I 1-392 Me i-Pr I 1-393 Et Me I 1-394 Et Et I 1-395 Et n-Pr I 1-396 Et i-Pr I 1-397 CF₃ Me I 1-398 CF₃ Et I 1-399 CF₃ n-Pr I 1-400 CF₃ i-Pr I 1-401 OMe Me I 1-402 OMe Et I 1-403 OMe n-Pr I 1-404 OMe i-Pr I 1-405 OEt Me I 1-406 OEt Et I 1-407 OEt n-Pr I 1-408 OEt i-Pr I 1-409 NO₂ Me I 1-410 NO₂ Et I 1-411 NO₂ n-Pr I 1-412 NO₂ i-Pr I 1-413 SO₂Me Me I 1-414 SO₂Me Et I 1-415 SO₂Me n-Pr I 1-416 SO₂Me i-Pr I 1-417 CH₂OMe Me I 1-418 CH₂OMe Et I 1-419 CH₂OMe n-Pr I 1-420 CH₂OMe i-Pr I 1-421 CH₂SO₂Me Me I 1-422 CH₂SO₂Me Et I 1-423 CH₂SO₂Me n-Pr I 1-424 CH₂SO₂Me i-Pr I 1-425 CH₂OCH₂CH₂OMe Me I 1-426 CH₂OCH₂CH₂OMe Et I 1-427 CH₂OCH₂CH₂OMe n-Pr I 1-428 CH₂OCH₂CH₂OMe i-Pr I 1-429 CH₂OCH₂CH₂OEt Me I 1-430 CH₂OCH₂CH₂OEt Et I 1-431 CH₂OCH₂CH₂OEt n-Pr I 1-432 CH₂OCH₂CH₂OEt i-Pr I 1-433 CH₂OCH₂CH₂CH₂OMe Me I 1-434 CH₂OCH₂CH₂CH₂OMe Et I 1-435 CH₂OCH₂CH₂CH₂OMe n-Pr I 1-436 CH₂OCH₂CH₂CH₂OMe i-Pr I 1-437 CH₂OCH₂OMe Me I 1-438 CH₂OCH₂OMe Et I 1-439 CH₂OCH₂OMe n-Pr I 1-440 CH₂OCH₂OMe i-Pr I 1-441 CH₂OCH₂OEt Me I 1-442 CH₂OCH₂OEt Et I 1-443 CH₂OCH₂OEt n-Pr I 1-444 CH₂OCH₂OEt i-Pr I 1-445 CH₂OCH₂CH₂SO₂Me Me I 1-446 CH₂OCH₂CH₂SO₂Me Et I 1-447 CH₂OCH₂CH₂SO₂Me n-Pr I 1-448 CH₂OCH₂CH₂SO₂Me i-Pr I 1-449 CH₂SO₂CH₂CH₂OMe Me I 1-450 CH₂SO₂CH₂CH₂OMe Et I 1-451 CH₂SO₂CH₂CH₂OMe n-Pr I 1-452 CH₂SO₂CH₂CH₂OMe i-Pr I 1-453 CH₂SO₂CH₂CH₂SO₂Me Me I 1-454 CH₂SO₂CH₂CH₂SO₂Me Et I 1-455 CH₂SO₂CH₂CH₂SO₂Me n-Pr I 1-456 CH₂SO₂CH₂CH₂SO₂Me i-Pr I 1-457 Cl Me NO₂ 1-458 Cl Et NO₂ 1-459 Cl n-Pr NO₂ 1-460 Cl i-Pr NO₂ 1-461 Br Me NO₂ 1-462 Br Et NO₂ 1-463 Br n-Pr NO₂ 1-464 Br i-Pr NO₂ 1-465 Me Me NO₂ 1-466 Me Et NO₂ 1-467 Me n-Pr NO₂ 1-468 Me i-Pr NO₂ 1-469 Et Me NO₂ 1-470 Et Et NO₂ 1-471 Et n-Pr NO₂ 1-472 Et i-Pr NO₂ 1-473 CF₃ Me NO₂ 1-474 CF₃ Et NO₂ 1-475 CF₃ n-Pr NO₂ 1-476 CF₃ i-Pr NO₂ 1-477 OMe Me NO₂ 1-478 OMe Et NO₂ 1-479 OMe n-Pr NO₂ 1-480 OMe i-Pr NO₂ 1-481 OEt Me NO₂ 1-482 OEt Et NO₂ 1-483 OEt n-Pr NO₂ 1-484 OEt i-Pr NO₂ 1-485 NO₂ Me NO₂ 1-486 NO₂ Et NO₂ 1-487 NO₂ n-Pr NO₂ 1-488 NO₂ i-Pr NO₂ 1-489 SO₂Me Me NO₂ 1-490 SO₂Me Et NO₂ 1-491 SO₂Me n-Pr NO₂ 1-492 SO₂Me i-Pr NO₂ 1-493 CH₂OMe Me NO₂ 1-494 CH₂OMe Et NO₂ 1-495 CH₂OMe n-Pr NO₂ 1-496 CH₂OMe i-Pr NO₂ 1-497 CH₂SO₂Me Me NO₂ 1-498 CH₂SO₂Me Et NO₂ 1-499 CH₂SO₂Me n-Pr NO₂ 1-500 CH₂SO₂Me i-Pr NO₂ 1-501 CH₂OCH₂CH₂OMe Me NO₂ 1-502 CH₂OCH₂CH₂OMe Et NO₂ 1-503 CH₂OCH₂CH₂OMe n-Pr NO₂ 1-504 CH₂OCH₂CH₂OMe i-Pr NO₂ 1-505 CH₂OCH₂CH₂OEt Me NO₂ 1-506 CH₂OCH₂CH₂OEt Et NO₂ 1-507 CH₂OCH₂CH₂OEt n-Pr NO₂ 1-508 CH₂OCH₂CH₂OEt i-Pr NO₂ 1-509 CH₂OCH₂CH₂CH₂OMe Me NO₂ 1-510 CH₂OCH₂CH₂CH₂OMe Et NO₂ 1-511 CH₂OCH₂CH₂CH₂OMe n-Pr NO₂ 1-512 CH₂OCH₂CH₂CH₂OMe i-Pr NO₂ 1-513 CH₂OCH₂OMe Me NO₂ 1-514 CH₂OCH₂OMe Et NO₂ 1-515 CH₂OCH₂OMe n-Pr NO₂ 1-516 CH₂OCH₂OMe i-Pr NO₂ 1-517 CH₂OCH₂OEt Me NO₂ 1-518 CH₂OCH₂OEt Et NO₂ 1-519 CH₂OCH₂OEt n-Pr NO₂ 1-520 CH₂OCH₂OEt i-Pr NO₂ 1-521 CH₂OCH₂CH₂SO₂Me Me NO₂ 1-522 CH₂OCH₂CH₂SO₂Me Et NO₂ 1-523 CH₂OCH₂CH₂SO₂Me n-Pr NO₂ 1-524 CH₂OCH₂CH₂SO₂Me i-Pr NO₂ 1-525 CH₂SO₂CH₂CH₂OMe Me NO₂ 1-526 CH₂SO₂CH₂CH₂OMe Et NO₂ 1-527 CH₂SO₂CH₂CH₂OMe n-Pr NO₂ 1-528 CH₂SO₂CH₂CH₂OMe i-Pr NO₂ 1-529 CH₂SO₂CH₂CH₂SO₂Me Me NO₂ 1-530 CH₂SO₂CH₂CH₂SO₂Me Et NO₂ 1-531 CH₂SO₂CH₂CH₂SO₂Me n-Pr NO₂ 1-532 CH₂SO₂CH₂CH₂SO₂Me i-Pr NO₂ The abbreviations used are: Et = ethyl Me = methyl Pr = propyl Ph = phenyl

TABLE 2 Compounds of the formula (I) according to the invention in which R¹ is ethyl, R² and R⁴ are each hydrogen.

Physical data: No. X R³ Y ¹H-NMR: δ [CDCl₃] 2-1 Cl Me SO₂Me 2-2 Cl Et SO₂Me 2-3 Cl n-Pr SO₂Me 2-4 Cl i-Pr SO₂Me 2-5 Br Me SO₂Me 2-6 Br Et SO₂Me 2-7 Br n-Pr SO₂Me 2-8 Br i-Pr SO₂Me 2-9 Me Me SO₂Me 8.08 (d, 1H), 7.62 (d, 1H), 7.28 (s, 1H), 4.09 (q, 2H), 3.38 (s, 3H), 3.18 (s, 3H), 2.88 (s, 3H), 1.46 (t, 3H) 2-10 Me Et SO₂Me 8.10 (d, 1H), 7.62 (d, 1H), 7.28 (s, 1H), 4.08 (q, 2H), 3.52 (m, 1H), 3.38 (s, 3H), 3.28 (m, 1H), 2.82 (s, 3H), 1.52 (t, 3H), 1.47 (t, 3H) 2-11 Me n-Pr SO₂Me 8.08 (d, 1H), 7.61 (d, 1H), 7.27 (s, 1H), 4.08 (q, 2H), 3.52 (m, 1H), 3.37 (s, 3H), 3.16 (m, 1H), 2.83 (s, 3H), 2.02 (m, 2H), 1.47 (t, 3H), 1.17 (t, 3H) 2-12 Me i-Pr SO₂Me 8.17 (m, 1H), 7.62 (d, 1H), 7.26 (s, 1H), 4.08 (q, 2H), 3.74 (m, 1H), 3.37 (s, 3H), 2.87 (s, 3H), 1.55 (d, 3H), 1.47 (t, 3H), 1.27 (m, 3H) 2-13 Et Me SO₂Me 2-14 Et Et SO₂Me 2-15 Et n-Pr SO₂Me 2-16 Et i-Pr SO₂Me 2-17 CF₃ Me SO₂Me 2-18 CF₃ Et SO₂Me 2-19 CF₃ n-Pr SO₂Me 2-20 CF₃ i-Pr SO₂Me 2-21 OMe Me SO₂Me 2-22 OMe Et SO₂Me 2-23 OMe n-Pr SO₂Me 2-24 OMe i-Pr SO₂Me 2-25 OEt Me SO₂Me 2-26 OEt Et SO₂Me 2-27 OEt n-Pr SO₂Me 2-28 OEt i-Pr SO₂Me 2-29 NO₂ Me SO₂Me 2-30 NO₂ Et SO₂Me 2-31 NO₂ n-Pr SO₂Me 2-32 NO₂ i-Pr SO₂Me 2-33 SO₂Me Me SO₂Me 2-34 SO₂Me Et SO₂Me 2-35 SO₂Me n-Pr SO₂Me 2-36 SO₂Me i-Pr SO₂Me 2-37 CH₂OMe Me SO₂Me 2-38 CH₂OMe Et SO₂Me 2-39 CH₂OMe n-Pr SO₂Me 2-40 CH₂OMe i-Pr SO₂Me 2-41 CH₂SO₂Me Me SO₂Me 2-42 CH₂SO₂Me Et SO₂Me 2-43 CH₂SO₂Me n-Pr SO₂Me 2-44 CH₂SO₂Me i-Pr SO₂Me 2-45 CH₂OCH₂CH₂OMe Me SO₂Me 2-46 CH₂OCH₂CH₂OMe Et SO₂Me 2-47 CH₂OCH₂CH₂OMe n-Pr SO₂Me 2-48 CH₂OCH₂CH₂OMe i-Pr SO₂Me 2-49 CH₂OCH₂CH₂OEt Me SO₂Me 8.22 (d, 1H), 7.67 (d, 1H), 7.38 (s, 1H), 5.60-5.10 (br. signal, 1H), 4.97 (d, 1H), 4.09 (q, 2H), 3.62- 3.56 (m, 1H), 3.56- 3.49 (m, 1H), 3.47- 3.32 (m, 4H), 3.37 (s, 3H), 3.33 (s, 3H), 1.46 (t, 3H), 1.12 (t, 3H) 2-50 CH₂OCH₂CH₂OEt Et SO₂Me 2-51 CH₂OCH₂CH₂OEt n-Pr SO₂Me 2-52 CH₂OCH₂CH₂OEt i-Pr SO₂Me 2-53 CH₂OCH₂CH₂CH₂OMe Me SO₂Me 2-54 CH₂OCH₂CH₂CH₂OMe Et SO₂Me 2-55 CH₂OCH₂CH₂CH₂OMe n-Pr SO₂Me 2-56 CH₂OCH₂CH₂CH₂OMe i-Pr SO₂Me 2-57 CH₂OCH₂OMe Me SO₂Me 2-58 CH₂OCH₂OMe Et SO₂Me 2-59 CH₂OCH₂OMe n-Pr SO₂Me 2-60 CH₂OCH₂OMe i-Pr SO₂Me 2-61 CH₂OCH₂OEt Me SO₂Me 2-62 CH₂OCH₂OEt Et SO₂Me 2-63 CH₂OCH₂OEt n-Pr SO₂Me 2-64 CH₂OCH₂OEt i-Pr SO₂Me 2-65 CH₂OCH₂CH₂SO₂Me Me SO₂Me 2-66 CH₂OCH₂CH₂SO₂Me Et SO₂Me 2-67 CH₂OCH₂CH₂SO₂Me n-Pr SO₂Me 2-68 CH₂OCH₂CH₂SO₂Me i-Pr SO₂Me 2-69 CH₂SO₂CH₂CH₂OMe Me SO₂Me 2-70 CH₂SO₂CH₂CH₂OMe Et SO₂Me 2-71 CH₂SO₂CH₂CH₂OMe n-Pr SO₂Me 2-72 CH₂SO₂CH₂CH₂OMe i-Pr SO₂Me 2-73 CH₂SO₂CH₂CH₂SO₂Me Me SO₂Me 2-74 CH₂SO₂CH₂CH₂SO₂Me Et SO₂Me 2-75 CH₂SO₂CH₂CH₂SO₂Me n-Pr SO₂Me 2-76 CH₂SO₂CH₂CH₂SO₂Me i-Pr SO₂Me 2-77 Cl Me SO₂Et 2-78 Cl Et SO₂Et 2-79 Cl n-Pr SO₂Et 2-80 Cl i-Pr SO₂Et 2-81 Br Me SO₂Et 2-82 Br Et SO₂Et 2-83 Br n-Pr SO₂Et 2-84 Br i-Pr SO₂Et 2-85 Me Me SO₂Et 2-86 Me Et SO₂Et 2-87 Me n-Pr SO₂Et 2-88 Me i-Pr SO₂Et 2-89 Et Me SO₂Et 2-90 Et Et SO₂Et 2-91 Et n-Pr SO₂Et 2-92 Et i-Pr SO₂Et 2-93 CF₃ Me SO₂Et 2-94 CF₃ Et SO₂Et 2-95 CF₃ n-Pr SO₂Et 2-96 CF₃ i-Pr SO₂Et 2-97 OMe Me SO₂Et 2-98 OMe Et SO₂Et 2-99 OMe n-Pr SO₂Et 2-100 OMe i-Pr SO₂Et 2-101 OEt Me SO₂Et 2-102 OEt Et SO₂Et 2-103 OEt n-Pr SO₂Et 2-104 OEt i-Pr SO₂Et 2-105 NO₂ Me SO₂Et 2-106 NO₂ Et SO₂Et 2-107 NO₂ n-Pr SO₂Et 2-108 NO₂ i-Pr SO₂Et 2-109 SO₂Me Me SO₂Et 2-110 SO₂Me Et SO₂Et 2-111 SO₂Me n-Pr SO₂Et 2-112 SO₂Me i-Pr SO₂Et 2-113 CH₂OMe Me SO₂Et 2-114 CH₂OMe Et SO₂Et 2-115 CH₂OMe n-Pr SO₂Et 2-116 CH₂OMe i-Pr SO₂Et 2-117 CH₂SO₂Me Me SO₂Et 2-118 CH₂SO₂Me Et SO₂Et 2-119 CH₂SO₂Me n-Pr SO₂Et 2-120 CH₂SO₂Me i-Pr SO₂Et 2-121 CH₂OCH₂CH₂OMe Me SO₂Et 2-122 CH₂OCH₂CH₂OMe Et SO₂Et 2-123 CH₂OCH₂CH₂OMe n-Pr SO₂Et 2-124 CH₂OCH₂CH₂OMe i-Pr SO₂Et 2-125 CH₂OCH₂CH₂OEt Me SO₂Et 2-126 CH₂OCH₂CH₂OEt Et SO₂Et 2-127 CH₂OCH₂CH₂OEt n-Pr SO₂Et 2-128 CH₂OCH₂CH₂OEt i-Pr SO₂Et 2-129 CH₂OCH₂CH₂CH₂OMe Me SO₂Et 2-130 CH₂OCH₂CH₂CH₂OMe Et SO₂Et 2-131 CH₂OCH₂CH₂CH₂OMe n-Pr SO₂Et 2-132 CH₂OCH₂CH₂CH₂OMe i-Pr SO₂Et 2-133 CH₂OCH₂OMe Me SO₂Et 2-134 CH₂OCH₂OMe Et SO₂Et 2-135 CH₂OCH₂OMe n-Pr SO₂Et 2-136 CH₂OCH₂OMe i-Pr SO₂Et 2-137 CH₂OCH₂OEt Me SO₂Et 2-138 CH₂OCH₂OEt Et SO₂Et 2-139 CH₂OCH₂OEt n-Pr SO₂Et 2-140 CH₂OCH₂OEt i-Pr SO₂Et 2-141 CH₂OCH₂CH₂SO₂Me Me SO₂Et 2-142 CH₂OCH₂CH₂SO₂Me Et SO₂Et 2-143 CH₂OCH₂CH₂SO₂Me n-Pr SO₂Et 2-144 CH₂OCH₂CH₂SO₂Me i-Pr SO₂Et 2-145 CH₂SO₂CH₂CH₂OMe Me SO₂Et 2-146 CH₂SO₂CH₂CH₂OMe Et SO₂Et 2-147 CH₂SO₂CH₂CH₂OMe n-Pr SO₂Et 2-148 CH₂SO₂CH₂CH₂OMe i-Pr SO₂Et 2-149 CH₂SO₂CH₂CH₂SO₂Me Me SO₂Et 2-150 CH₂SO₂CH₂CH₂SO₂Me Et SO₂Et 2-151 CH₂SO₂CH₂CH₂SO₂Me n-Pr SO₂Et 2-152 CH₂SO₂CH₂CH₂SO₂Me i-Pr SO₂Et 2-153 Cl Me F 2-154 Cl Et F 2-155 Cl n-Pr F 2-156 Cl i-Pr F 2-157 Br Me F 2-158 Br Et F 2-159 Br n-Pr F 2-160 Br i-Pr F 2-161 Me Me F 2-162 Me Et F 2-163 Me n-Pr F 2-164 Me i-Pr F 2-165 Et Me F 2-166 Et Et F 2-167 Et n-Pr F 2-168 Et i-Pr F 2-169 CF₃ Me F 2-170 CF₃ Et F 2-171 CF₃ n-Pr F 2-172 CF₃ i-Pr F 2-173 OMe Me F 2-174 OMe Et F 2-175 OMe n-Pr F 2-176 OMe i-Pr F 2-177 OEt Me F 2-178 OEt Et F 2-179 OEt n-Pr F 2-180 OEt i-Pr F 2-181 NO₂ Me F 2-182 NO₂ Et F 2-183 NO₂ n-Pr F 2-184 NO₂ i-Pr F 2-185 SO₂Me Me F 2-186 SO₂Me Et F 2-187 SO₂Me n-Pr F 2-188 SO₂Me i-Pr F 2-189 CH₂OMe Me F 2-190 CH₂OMe Et F 2-191 CH₂OMe n-Pr F 2-192 CH₂OMe i-Pr F 2-193 CH₂SO₂Me Me F 2-194 CH₂SO₂Me Et F 2-195 CH₂SO₂Me n-Pr F 2-196 CH₂SO₂Me i-Pr F 2-197 CH₂OCH₂CH₂OMe Me F 2-198 CH₂OCH₂CH₂OMe Et F 2-199 CH₂OCH₂CH₂OMe n-Pr F 2-200 CH₂OCH₂CH₂OMe i-Pr F 2-201 CH₂OCH₂CH₂OEt Me F 2-202 CH₂OCH₂CH₂OEt Et F 2-203 CH₂OCH₂CH₂OEt n-Pr F 2-204 CH₂OCH₂CH₂OEt i-Pr F 2-205 CH₂OCH₂CH₂CH₂OMe Me F 2-206 CH₂OCH₂CH₂CH₂OMe Et F 2-207 CH₂OCH₂CH₂CH₂OMe n-Pr F 2-208 CH₂OCH₂CH₂CH₂OMe i-Pr F 2-209 CH₂OCH₂OMe Me F 2-210 CH₂OCH₂OMe Et F 2-211 CH₂OCH₂OMe n-Pr F 2-212 CH₂OCH₂OMe i-Pr F 2-213 CH₂OCH₂OEt Me F 2-214 CH₂OCH₂OEt Et F 2-215 CH₂OCH₂OEt n-Pr F 2-216 CH₂OCH₂OEt i-Pr F 2-217 CH₂OCH₂CH₂SO₂Me Me F 2-218 CH₂OCH₂CH₂SO₂Me Et F 2-219 CH₂OCH₂CH₂SO₂Me n-Pr F 2-220 CH₂OCH₂CH₂SO₂Me i-Pr F 2-221 CH₂SO₂CH₂CH₂OMe Me F 2-222 CH₂SO₂CH₂CH₂OMe Et F 2-223 CH₂SO₂CH₂CH₂OMe n-Pr F 2-224 CH₂SO₂CH₂CH₂OMe i-Pr F 2-225 CH₂SO₂CH₂CH₂SO₂Me Me F 2-226 CH₂SO₂CH₂CH₂SO₂Me Et F 2-227 CH₂SO₂CH₂CH₂SO₂Me n-Pr F 2-228 CH₂SO₂CH₂CH₂SO₂Me i-Pr F 2-229 Cl Me Cl 2-230 Cl Et Cl 2-231 Cl n-Pr Cl 2-232 Cl i-Pr Cl 2-233 Br Me Cl 2-234 Br Et Cl 2-235 Br n-Pr Cl 2-236 Br i-Pr Cl 2-237 Me Me Cl 7.43 (d, 1H), 7.37 (d, 1H), 7.33 (s, 1H), 4.08 (q, 2H), 3.03 (s, 3H), 2.73 (s, 3H), 1.45 (t, 3H) 2-238 Me Et Cl 7.41 (d, 1H), 7.36 (d, 1H), 7.32 (s, 1H), 4.07 (q, 2H), 3.38 (m, 1H), 3.17 (m, 1H), 2.72 (s, 3H), 1.46 (t, 3H), 1.41 (t, 3H) 2-239 Me n-Pr Cl 2-240 Me i-Pr Cl 2-241 Et Me Cl 2-242 Et Et Cl 2-243 Et n-Pr Cl 2-244 Et i-Pr Cl 2-245 CF₃ Me Cl 2-246 CF₃ Et Cl 2-247 CF₃ n-Pr Cl 2-248 CF₃ i-Pr Cl 2-249 OMe Me Cl 2-250 OMe Et Cl 2-251 OMe n-Pr Cl 2-252 OMe i-Pr Cl 2-253 OEt Me Cl 2-254 OEt Et Cl 2-255 OEt n-Pr Cl 2-256 OEt i-Pr Cl 2-257 NO₂ Me Cl 2-258 NO₂ Et Cl 2-259 NO₂ n-Pr Cl 2-260 NO₂ i-Pr Cl 2-261 SO₂Me Me Cl 2-262 SO₂Me Et Cl 2-263 SO₂Me n-Pr Cl 2-264 SO₂Me i-Pr Cl 2-265 CH₂OMe Me Cl 2-266 CH₂OMe Et Cl 2-267 CH₂OMe n-Pr Cl 2-268 CH₂OMe i-Pr Cl 2-269 CH₂SO₂Me Me Cl 2-270 CH₂SO₂Me Et Cl 2-271 CH₂SO₂Me n-Pr Cl 2-272 CH₂SO₂Me i-Pr Cl 2-273 CH₂OCH₂CH₂OMe Me Cl 2-274 CH₂OCH₂CH₂OMe Et Cl 2-275 CH₂OCH₂CH₂OMe n-Pr Cl 2-276 CH₂OCH₂CH₂OMe i-Pr Cl 2-277 CH₂OCH₂CH₂OEt Me Cl 2-278 CH₂OCH₂CH₂OEt Et Cl 2-279 CH₂OCH₂CH₂OEt n-Pr Cl 2-280 CH₂OCH₂CH₂OEt i-Pr Cl 2-281 CH₂OCH₂CH₂CH₂OMe Me Cl 2-282 CH₂OCH₂CH₂CH₂OMe Et Cl 2-283 CH₂OCH₂CH₂CH₂OMe n-Pr Cl 2-284 CH₂OCH₂CH₂CH₂OMe i-Pr Cl 2-285 CH₂OCH₂OMe Me Cl 2-286 CH₂OCH₂OMe Et Cl 2-287 CH₂OCH₂OMe n-Pr Cl 2-288 CH₂OCH₂OMe i-Pr Cl 2-289 CH₂OCH₂OEt Me Cl 2-290 CH₂OCH₂OEt Et Cl 2-291 CH₂OCH₂OEt n-Pr Cl 2-292 CH₂OCH₂OEt i-Pr Cl 2-293 CH₂OCH₂CH₂SO₂Me Me Cl 2-294 CH₂OCH₂CH₂SO₂Me Et Cl 2-295 CH₂OCH₂CH₂SO₂Me n-Pr Cl 2-296 CH₂OCH₂CH₂SO₂Me i-Pr Cl 2-297 CH₂SO₂CH₂CH₂OMe Me Cl 2-298 CH₂SO₂CH₂CH₂OMe Et Cl 2-299 CH₂SO₂CH₂CH₂OMe n-Pr Cl 2-300 CH₂SO₂CH₂CH₂OMe i-Pr Cl 2-301 CH₂SO₂CH₂CH₂SO₂Me Me Cl 2-302 CH₂SO₂CH₂CH₂SO₂Me Et Cl 2-303 CH₂SO₂CH₂CH₂SO₂Me n-Pr Cl 2-304 CH₂SO₂CH₂CH₂SO₂Me i-Pr Cl 2-305 Cl Me Br 2-306 Cl Et Br 2-307 Cl n-Pr Br 2-308 Cl i-Pr Br 2-309 Br Me Br 2-310 Br Et Br 2-311 Br n-Pr Br 2-312 Br i-Pr Br 2-313 Me Me Br 7.56 (d, 1H), 7.35 (s, 1H), 7.33 (d, 1H), 4.09 (q, 2H), 3.03 (s, 3H), 2.77 (s, 3H), 1.46 (t, 3H) 2-314 Me Et Br 2-315 Me n-Pr Br 2-316 Me i-Pr Br 2-317 Et Me Br 2-318 Et Et Br 2-319 Et n-Pr Br 2-320 Et i-Pr Br 2-321 CF₃ Me Br 2-322 CF₃ Et Br 2-323 CF₃ n-Pr Br 2-324 CF₃ i-Pr Br 2-325 OMe Me Br 2-326 OMe Et Br 2-327 OMe n-Pr Br 2-328 OMe i-Pr Br 2-329 OEt Me Br 2-330 OEt Et Br 2-331 OEt n-Pr Br 2-332 OEt i-Pr Br 2-333 NO₂ Me Br 2-334 NO₂ Et Br 2-335 NO₂ n-Pr Br 2-336 NO₂ i-Pr Br 2-337 SO₂Me Me Br 2-338 SO₂Me Et Br 2-339 SO₂Me n-Pr Br 2-340 SO₂Me i-Pr Br 2-341 CH₂OMe Me Br 2-342 CH₂OMe Et Br 2-343 CH₂OMe n-Pr Br 2-344 CH₂OMe i-Pr Br 2-345 CH₂SO₂Me Me Br 2-346 CH₂SO₂Me Et Br 2-347 CH₂SO₂Me n-Pr Br 2-348 CH₂SO₂Me i-Pr Br 2-349 CH₂OCH₂CH₂OMe Me Br 2-350 CH₂OCH₂CH₂OMe Et Br 2-351 CH₂OCH₂CH₂OMe n-Pr Br 2-352 CH₂OCH₂CH₂OMe i-Pr Br 2-353 CH₂OCH₂CH₂OEt Me Br 2-354 CH₂OCH₂CH₂OEt Et Br 2-355 CH₂OCH₂CH₂OEt n-Pr Br 2-356 CH₂OCH₂CH₂OEt i-Pr Br 2-357 CH₂OCH₂CH₂CH₂OMe Me Br 2-358 CH₂OCH₂CH₂CH₂OMe Et Br 2-359 CH₂OCH₂CH₂CH₂OMe n-Pr Br 2-360 CH₂OCH₂CH₂CH₂OMe i-Pr Br 2-361 CH₂OCH₂OMe Me Br 2-362 CH₂OCH₂OMe Et Br 2-363 CH₂OCH₂OMe n-Pr Br 2-364 CH₂OCH₂OMe i-Pr Br 2-365 CH₂OCH₂OEt Me Br 2-366 CH₂OCH₂OEt Et Br 2-367 CH₂OCH₂OEt n-Pr Br 2-368 CH₂OCH₂OEt i-Pr Br 2-369 CH₂OCH₂CH₂SO₂Me Me Br 2-370 CH₂OCH₂CH₂SO₂Me Et Br 2-371 CH₂OCH₂CH₂SO₂Me n-Pr Br 2-372 CH₂OCH₂CH₂SO₂Me i-Pr Br 2-373 CH₂SO₂CH₂CH₂OMe Me Br 2-374 CH₂SO₂CH₂CH₂OMe Et Br 2-375 CH₂SO₂CH₂CH₂OMe n-Pr Br 2-376 CH₂SO₂CH₂CH₂OMe i-Pr Br 2-377 CH₂SO₂CH₂CH₂SO₂Me Me Br 2-378 CH₂SO₂CH₂CH₂SO₂Me Et Br 2-379 CH₂SO₂CH₂CH₂SO₂Me n-Pr Br 2-380 CH₂SO₂CH₂CH₂SO₂Me i-Pr Br 2-381 Cl Me I 2-382 Cl Et I 2-383 Cl n-Pr I 2-384 Cl i-Pr I 2-385 Br Me I 2-386 Br Et I 2-387 Br n-Pr I 2-388 Br i-Pr I 2-389 Me Me I 7.87 (d, 1H), 7.31 (s, 1H), 7.12 (d, 1H), 4.08 (q, 2H), 2.97 (s, 3H), 2.77 (s, 3H), 1.45 (t, 3H) 2-390 Me Et I 2-391 Me n-Pr I 2-392 Me i-Pr I 2-393 Et Me I 2-394 Et Et I 2-395 Et n-Pr I 2-396 Et i-Pr I 2-397 CF₃ Me I 2-398 CF₃ Et I 2-399 CF₃ n-Pr I 2-400 CF₃ i-Pr I 2-401 OMe Me I 2-402 OMe Et I 2-403 OMe n-Pr I 2-404 OMe i-Pr I 2-405 OEt Me I 2-406 OEt Et I 2-407 OEt n-Pr I 2-408 OEt i-Pr I 2-409 NO₂ Me I 2-410 NO₂ Et I 2-411 NO₂ n-Pr I 2-412 NO₂ i-Pr I 2-413 SO₂Me Me I 2-414 SO₂Me Et I 2-415 SO₂Me n-Pr I 2-416 SO₂Me i-Pr I 2-417 CH₂OMe Me I 2-418 CH₂OMe Et I 2-419 CH₂OMe n-Pr I 2-420 CH₂OMe i-Pr I 2-421 CH₂SO₂Me Me I 2-422 CH₂SO₂Me Et I 2-423 CH₂SO₂Me n-Pr I 2-424 CH₂SO₂Me i-Pr I 2-425 CH₂OCH₂CH₂OMe Me I 2-426 CH₂OCH₂CH₂OMe Et I 2-427 CH₂OCH₂CH₂OMe n-Pr I 2-428 CH₂OCH₂CH₂OMe i-Pr I 2-429 CH₂OCH₂CH₂OEt Me I 2-430 CH₂OCH₂CH₂OEt Et I 2-431 CH₂OCH₂CH₂OEt n-Pr I 2-432 CH₂OCH₂CH₂OEt i-Pr I 2-433 CH₂OCH₂CH₂CH₂OMe Me I 2-434 CH₂OCH₂CH₂CH₂OMe Et I 2-435 CH₂OCH₂CH₂CH₂OMe n-Pr I 2-436 CH₂OCH₂CH₂CH₂OMe i-Pr I 2-437 CH₂OCH₂OMe Me I 2-438 CH₂OCH₂OMe Et I 2-439 CH₂OCH₂OMe n-Pr I 2-440 CH₂OCH₂OMe i-Pr I 2-441 CH₂OCH₂OEt Me I 2-442 CH₂OCH₂OEt Et I 2-443 CH₂OCH₂OEt n-Pr I 2-444 CH₂OCH₂OEt i-Pr I 2-445 CH₂OCH₂CH₂SO₂Me Me I 2-446 CH₂OCH₂CH₂SO₂Me Et I 2-447 CH₂OCH₂CH₂SO₂Me n-Pr I 2-448 CH₂OCH₂CH₂SO₂Me i-Pr I 2-449 CH₂SO₂CH₂CH₂OMe Me I 2-450 CH₂SO₂CH₂CH₂OMe Et I 2-451 CH₂SO₂CH₂CH₂OMe n-Pr I 2-452 CH₂SO₂CH₂CH₂OMe i-Pr I 2-453 CH₂SO₂CH₂CH₂SO₂Me Me I 2-454 CH₂SO₂CH₂CH₂SO₂Me Et I 2-455 CH₂SO₂CH₂CH₂SO₂Me n-Pr I 2-456 CH₂SO₂CH₂CH₂SO₂Me i-Pr I 2-457 Cl Me NO₂ 2-458 Cl Et NO₂ 2-459 Cl n-Pr NO₂ 2-460 Cl i-Pr NO₂ 2-461 Br Me NO₂ 2-462 Br Et NO₂ 2-463 Br n-Pr NO₂ 2-464 Br i-Pr NO₂ 2-465 Me Me NO₂ 2-466 Me Et NO₂ 2-467 Me n-Pr NO₂ 2-468 Me i-Pr NO₂ 2-469 Et Me NO₂ 2-470 Et Et NO₂ 2-471 Et n-Pr NO₂ 2-472 Et i-Pr NO₂ 2-473 CF₃ Me NO₂ 2-474 CF₃ Et NO₂ 2-475 CF₃ n-Pr NO₂ 2-476 CF₃ i-Pr NO₂ 2-477 OMe Me NO₂ 2-478 OMe Et NO₂ 2-479 OMe n-Pr NO₂ 2-480 OMe i-Pr NO₂ 2-481 OEt Me NO₂ 2-482 OEt Et NO₂ 2-483 OEt n-Pr NO₂ 2-484 OEt i-Pr NO₂ 2-485 NO₂ Me NO₂ 2-486 NO₂ Et NO₂ 2-487 NO₂ n-Pr NO₂ 2-488 NO₂ i-Pr NO₂ 2-489 SO₂Me Me NO₂ 2-490 SO₂Me Et NO₂ 2-491 SO₂Me n-Pr NO₂ 2-492 SO₂Me i-Pr NO₂ 2-493 CH₂OMe Me NO₂ 2-494 CH₂OMe Et NO₂ 2-495 CH₂OMe n-Pr NO₂ 2-496 CH₂OMe i-Pr NO₂ 2-497 CH₂SO₂Me Me NO₂ 2-498 CH₂SO₂Me Et NO₂ 2-499 CH₂SO₂Me n-Pr NO₂ 2-500 CH₂SO₂Me i-Pr NO₂ 2-501 CH₂OCH₂CH₂OMe Me NO₂ 2-502 CH₂OCH₂CH₂OMe Et NO₂ 2-503 CH₂OCH₂CH₂OMe n-Pr NO₂ 2-504 CH₂OCH₂CH₂OMe i-Pr NO₂ 2-505 CH₂OCH₂CH₂OEt Me NO₂ 2-506 CH₂OCH₂CH₂OEt Et NO₂ 2-507 CH₂OCH₂CH₂OEt n-Pr NO₂ 2-508 CH₂OCH₂CH₂OEt i-Pr NO₂ 2-509 CH₂OCH₂CH₂CH₂OMe Me NO₂ 2-510 CH₂OCH₂CH₂CH₂OMe Et NO₂ 2-511 CH₂OCH₂CH₂CH₂OMe n-Pr NO₂ 2-512 CH₂OCH₂CH₂CH₂OMe i-Pr NO₂ 2-513 CH₂OCH₂OMe Me NO₂ 2-514 CH₂OCH₂OMe Et NO₂ 2-515 CH₂OCH₂OMe n-Pr NO₂ 2-516 CH₂OCH₂OMe i-Pr NO₂ 2-517 CH₂OCH₂OEt Me NO₂ 2-518 CH₂OCH₂OEt Et NO₂ 2-519 CH₂OCH₂OEt n-Pr NO₂ 2-520 CH₂OCH₂OEt i-Pr NO₂ 2-521 CH₂OCH₂CH₂SO₂Me Me NO₂ 2-522 CH₂OCH₂CH₂SO₂Me Et NO₂ 2-523 CH₂OCH₂CH₂SO₂Me n-Pr NO₂ 2-524 CH₂OCH₂CH₂SO₂Me i-Pr NO₂ 2-525 CH₂SO₂CH₂CH₂OMe Me NO₂ 2-526 CH₂SO₂CH₂CH₂OMe Et NO₂ 2-527 CH₂SO₂CH₂CH₂OMe n-Pr NO₂ 2-528 CH₂SO₂CH₂CH₂OMe i-Pr NO₂ 2-529 CH₂SO₂CH₂CH₂SO₂Me Me NO₂ 2-530 CH₂SO₂CH₂CH₂SO₂Me Et NO₂ 2-531 CH₂SO₂CH₂CH₂SO₂Me n-Pr NO₂ 2-532 CH₂SO₂CH₂CH₂SO₂Me i-Pr NO₂

TABLE 3 Compounds of the formula (I) according to the invention in which R⁴ is hydrogen and R¹ and R² are each methyl.

Physical data: No. X R³ Y ¹H-NMR: δ [CDCl₃] 3-1 Cl Me SO₂Me 3-2 Cl Et SO₂Me 3-3 Cl n-Pr SO₂Me 3-4 Cl i-Pr SO₂Me 3-5 Br Me SO₂Me 3-6 Br Et SO₂Me 3-7 Br n-Pr SO₂Me 3-8 Br i-Pr SO₂Me 3-9 Me Me SO₂Me 8.09 (d, 1H), 7.49 (d, 1H), 3.64 (s, 3H), 3.38 (s, 3H), 3.18 (s, 3H), 2.81 (s, 3H), 1.69 (s, 3H) 3-10 Me Et SO₂Me 3-11 Me n-Pr SO₂Me 3-12 Me i-Pr SO₂Me 3-13 Et Me SO₂Me 3-14 Et Et SO₂Me 3-15 Et n-Pr SO₂Me 3-16 Et i-Pr SO₂Me 3-17 CF₃ Me SO₂Me 3-18 CF₃ Et SO₂Me 3-19 CF₃ n-Pr SO₂Me 3-20 CF₃ i-Pr SO₂Me 3-21 OMe Me SO₂Me 3-22 OMe Et SO₂Me 3-23 OMe n-Pr SO₂Me 3-24 OMe i-Pr SO₂Me 3-25 OEt Me SO₂Me 3-26 OEt Et SO₂Me 3-27 OEt n-Pr SO₂Me 3-28 OEt i-Pr SO₂Me 3-29 NO₂ Me SO₂Me 3-30 NO₂ Et SO₂Me 3-31 NO₂ n-Pr SO₂Me 3-32 NO₂ i-Pr SO₂Me 3-33 SO₂Me Me SO₂Me 3-34 SO₂Me Et SO₂Me 3-35 SO₂Me n-Pr SO₂Me 3-36 SO₂Me i-Pr SO₂Me 3-37 CH₂OMe Me SO₂Me 3-38 CH₂OMe Et SO₂Me 3-39 CH₂OMe n-Pr SO₂Me 3-40 CH₂OMe i-Pr SO₂Me 3-41 CH₂SO₂Me Me SO₂Me 3-42 CH₂SO₂Me Et SO₂Me 3-43 CH₂SO₂Me n-Pr SO₂Me 3-44 CH₂SO₂Me i-Pr SO₂Me 3-45 CH₂OCH₂CH₂OMe Me SO₂Me 3-46 CH₂OCH₂CH₂OMe Et SO₂Me 3-47 CH₂OCH₂CH₂OMe n-Pr SO₂Me 3-48 CH₂OCH₂CH₂OMe i-Pr SO₂Me 3-49 CH₂OCH₂CH₂OEt Me SO₂Me 3-50 CH₂OCH₂CH₂OEt Et SO₂Me 3-51 CH₂OCH₂CH₂OEt n-Pr SO₂Me 3-52 CH₂OCH₂CH₂OEt i-Pr SO₂Me 3-53 CH₂OCH₂CH₂CH₂OMe Me SO₂Me 3-54 CH₂OCH₂CH₂CH₂OMe Et SO₂Me 3-55 CH₂OCH₂CH₂CH₂OMe n-Pr SO₂Me 3-56 CH₂OCH₂CH₂CH₂OMe i-Pr SO₂Me 3-57 CH₂OCH₂OMe Me SO₂Me 3-58 CH₂OCH₂OMe Et SO₂Me 3-59 CH₂OCH₂OMe n-Pr SO₂Me 3-60 CH₂OCH₂OMe i-Pr SO₂Me 3-61 CH₂OCH₂OEt Me SO₂Me 3-62 CH₂OCH₂OEt Et SO₂Me 3-63 CH₂OCH₂OEt n-Pr SO₂Me 3-64 CH₂OCH₂OEt i-Pr SO₂Me 3-65 CH₂OCH₂CH₂SO₂Me Me SO₂Me 3-66 CH₂OCH₂CH₂SO₂Me Et SO₂Me 3-67 CH₂OCH₂CH₂SO₂Me n-Pr SO₂Me 3-68 CH₂OCH₂CH₂SO₂Me i-Pr SO₂Me 3-69 CH₂SO₂CH₂CH₂OMe Me SO₂Me 3-70 CH₂SO₂CH₂CH₂OMe Et SO₂Me 3-71 CH₂SO₂CH₂CH₂OMe n-Pr SO₂Me 3-72 CH₂SO₂CH₂CH₂OMe i-Pr SO₂Me 3-73 CH₂SO₂CH₂CH₂SO₂Me Me SO₂Me 3-74 CH₂SO₂CH₂CH₂SO₂Me Et SO₂Me 3-75 CH₂SO₂CH₂CH₂SO₂Me n-Pr SO₂Me 3-76 CH₂SO₂CH₂CH₂SO₂Me i-Pr SO₂Me 3-77 Cl Me SO₂Et 3-78 Cl Et SO₂Et 3-79 Cl n-Pr SO₂Et 3-80 Cl i-Pr SO₂Et 3-81 Br Me SO₂Et 3-82 Br Et SO₂Et 3-83 Br n-Pr SO₂Et 3-84 Br i-Pr SO₂Et 3-85 Me Me SO₂Et 3-86 Me Et SO₂Et 3-87 Me n-Pr SO₂Et 3-88 Me i-Pr SO₂Et 3-89 Et Me SO₂Et 3-90 Et Et SO₂Et 3-91 Et n-Pr SO₂Et 3-92 Et i-Pr SO₂Et 3-93 CF₃ Me SO₂Et 3-94 CF₃ Et SO₂Et 3-95 CF₃ n-Pr SO₂Et 3-96 CF₃ i-Pr SO₂Et 3-97 OMe Me SO₂Et 3-98 OMe Et SO₂Et 3-99 OMe n-Pr SO₂Et 3-100 OMe i-Pr SO₂Et 3-101 OEt Me SO₂Et 3-102 OEt Et SO₂Et 3-103 OEt n-Pr SO₂Et 3-104 OEt i-Pr SO₂Et 3-105 NO₂ Me SO₂Et 3-106 NO₂ Et SO₂Et 3-107 NO₂ n-Pr SO₂Et 3-108 NO₂ i-Pr SO₂Et 3-109 SO₂Me Me SO₂Et 3-110 SO₂Me Et SO₂Et 3-111 SO₂Me n-Pr SO₂Et 3-112 SO₂Me i-Pr SO₂Et 3-113 CH₂OMe Me SO₂Et 3-114 CH₂OMe Et SO₂Et 3-115 CH₂OMe n-Pr SO₂Et 3-116 CH₂OMe i-Pr SO₂Et 3-117 CH₂SO₂Me Me SO₂Et 3-118 CH₂SO₂Me Et SO₂Et 3-119 CH₂SO₂Me n-Pr SO₂Et 3-120 CH₂SO₂Me i-Pr SO₂Et 3-121 CH₂OCH₂CH₂OMe Me SO₂Et 3-122 CH₂OCH₂CH₂OMe Et SO₂Et 3-123 CH₂OCH₂CH₂OMe n-Pr SO₂Et 3-124 CH₂OCH₂CH₂OMe i-Pr SO₂Et 3-125 CH₂OCH₂CH₂OEt Me SO₂Et 3-126 CH₂OCH₂CH₂OEt Et SO₂Et 3-127 CH₂OCH₂CH₂OEt n-Pr SO₂Et 3-128 CH₂OCH₂CH₂OEt i-Pr SO₂Et 3-129 CH₂OCH₂CH₂CH₂OMe Me SO₂Et 3-130 CH₂OCH₂CH₂CH₂OMe Et SO₂Et 3-131 CH₂OCH₂CH₂CH₂OMe n-Pr SO₂Et 3-132 CH₂OCH₂CH₂CH₂OMe i-Pr SO₂Et 3-133 CH₂OCH₂OMe Me SO₂Et 3-134 CH₂OCH₂OMe Et SO₂Et 3-135 CH₂OCH₂OMe n-Pr SO₂Et 3-136 CH₂OCH₂OMe i-Pr SO₂Et 3-137 CH₂OCH₂OEt Me SO₂Et 3-138 CH₂OCH₂OEt Et SO₂Et 3-139 CH₂OCH₂OEt n-Pr SO₂Et 3-140 CH₂OCH₂OEt i-Pr SO₂Et 3-141 CH₂OCH₂CH₂SO₂Me Me SO₂Et 3-142 CH₂OCH₂CH₂SO₂Me Et SO₂Et 3-143 CH₂OCH₂CH₂SO₂Me n-Pr SO₂Et 3-144 CH₂OCH₂CH₂SO₂Me i-Pr SO₂Et 3-145 CH₂SO₂CH₂CH₂OMe Me SO₂Et 3-146 CH₂SO₂CH₂CH₂OMe Et SO₂Et 3-147 CH₂SO₂CH₂CH₂OMe n-Pr SO₂Et 3-148 CH₂SO₂CH₂CH₂OMe i-Pr SO₂Et 3-149 CH₂SO₂CH₂CH₂SO₂Me Me SO₂Et 3-150 CH₂SO₂CH₂CH₂SO₂Me Et SO₂Et 3-151 CH₂SO₂CH₂CH₂SO₂Me n-Pr SO₂Et 3-152 CH₂SO₂CH₂CH₂SO₂Me i-Pr SO₂Et 3-153 Cl Me F 3-154 Cl Et F 3-155 Cl n-Pr F 3-156 Cl i-Pr F 3-157 Br Me F 3-158 Br Et F 3-159 Br n-Pr F 3-160 Br i-Pr F 3-161 Me Me F 3-162 Me Et F 3-163 Me n-Pr F 3-164 Me i-Pr F 3-165 Et Me F 3-166 Et Et F 3-167 Et n-Pr F 3-168 Et i-Pr F 3-169 CF₃ Me F 3-170 CF₃ Et F 3-171 CF₃ n-Pr F 3-172 CF₃ i-Pr F 3-173 OMe Me F 3-174 OMe Et F 3-175 OMe n-Pr F 3-176 OMe i-Pr F 3-177 OEt Me F 3-178 OEt Et F 3-179 OEt n-Pr F 3-180 OEt i-Pr F 3-181 NO₂ Me F 3-182 NO₂ Et F 3-183 NO₂ n-Pr F 3-184 NO₂ i-Pr F 3-185 SO₂Me Me F 3-186 SO₂Me Et F 3-187 SO₂Me n-Pr F 3-188 SO₂Me i-Pr F 3-189 CH₂OMe Me F 3-190 CH₂OMe Et F 3-191 CH₂OMe n-Pr F 3-192 CH₂OMe i-Pr F 3-193 CH₂SO₂Me Me F 3-194 CH₂SO₂Me Et F 3-195 CH₂SO₂Me n-Pr F 3-196 CH₂SO₂Me i-Pr F 3-197 CH₂OCH₂CH₂OMe Me F 3-198 CH₂OCH₂CH₂OMe Et F 3-199 CH₂OCH₂CH₂OMe n-Pr F 3-200 CH₂OCH₂CH₂OMe i-Pr F 3-201 CH₂OCH₂CH₂OEt Me F 3-202 CH₂OCH₂CH₂OEt Et F 3-203 CH₂OCH₂CH₂OEt n-Pr F 3-204 CH₂OCH₂CH₂OEt i-Pr F 3-205 CH₂OCH₂CH₂CH₂OMe Me F 3-206 CH₂OCH₂CH₂CH₂OMe Et F 3-207 CH₂OCH₂CH₂CH₂OMe n-Pr F 3-208 CH₂OCH₂CH₂CH₂OMe i-Pr F 3-209 CH₂OCH₂OMe Me F 3-210 CH₂OCH₂OMe Et F 3-211 CH₂OCH₂OMe n-Pr F 3-212 CH₂OCH₂OMe i-Pr F 3-213 CH₂OCH₂OEt Me F 3-214 CH₂OCH₂OEt Et F 3-215 CH₂OCH₂OEt n-Pr F 3-216 CH₂OCH₂OEt i-Pr F 3-217 CH₂OCH₂CH₂SO₂Me Me F 3-218 CH₂OCH₂CH₂SO₂Me Et F 3-219 CH₂OCH₂CH₂SO₂Me n-Pr F 3-220 CH₂OCH₂CH₂SO₂Me i-Pr F 3-221 CH₂SO₂CH₂CH₂OMe Me F 3-222 CH₂SO₂CH₂CH₂OMe Et F 3-223 CH₂SO₂CH₂CH₂OMe n-Pr F 3-224 CH₂SO₂CH₂CH₂OMe i-Pr F 3-225 CH₂SO₂CH₂CH₂SO₂Me Me F 3-226 CH₂SO₂CH₂CH₂SO₂Me Et F 3-227 CH₂SO₂CH₂CH₂SO₂Me n-Pr F 3-228 CH₂SO₂CH₂CH₂SO₂Me i-Pr F 3-229 Cl Me Cl 3-230 Cl Et Cl 3-231 Cl n-Pr Cl 3-232 Cl i-Pr Cl 3-233 Br Me Cl 3-234 Br Et Cl 3-235 Br n-Pr Cl 3-236 Br i-Pr Cl 3-237 Me Me Cl 7.37 (d, 1H), 7.23 (d, 1H), 3.63 (s, 3H), 3.01 (s, 3H), 2.68 (s, 3H), 1.72 (s, 3H) 3-238 Me Et Cl 7.37 (d, 1H), 7.23 (d, 1H), 3.63 (s, 3H), 3.36 (m, 1H), 3.16 (m, 1H), 2.63 (s, 3H), 1.72 (s, 3H), 1.40 (t, 3H) 3-239 Me n-Pr Cl 3-240 Me i-Pr Cl 3-241 Et Me Cl 3-242 Et Et Cl 3-243 Et n-Pr Cl 3-244 Et i-Pr Cl 3-245 CF₃ Me Cl 3-246 CF₃ Et Cl 3-247 CF₃ n-Pr Cl 3-248 CF₃ i-Pr Cl 3-249 OMe Me Cl 3-250 OMe Et Cl 3-251 OMe n-Pr Cl 3-252 OMe i-Pr Cl 3-253 OEt Me Cl 3-254 OEt Et Cl 3-255 OEt n-Pr Cl 3-256 OEt i-Pr Cl 3-257 NO₂ Me Cl 3-258 NO₂ Et Cl 3-259 NO₂ n-Pr Cl 3-260 NO₂ i-Pr Cl 3-261 SO₂Me Me Cl 3-262 SO₂Me Et Cl 3-263 SO₂Me n-Pr Cl 3-264 SO₂Me i-Pr Cl 3-265 CH₂OMe Me Cl 3-266 CH₂OMe Et Cl 3-267 CH₂OMe n-Pr Cl 3-268 CH₂OMe i-Pr Cl 3-269 CH₂SO₂Me Me Cl 3-270 CH₂SO₂Me Et Cl 3-271 CH₂SO₂Me n-Pr Cl 3-272 CH₂SO₂Me i-Pr Cl 3-273 CH₂OCH₂CH₂OMe Me Cl 3-274 CH₂OCH₂CH₂OMe Et Cl 3-275 CH₂OCH₂CH₂OMe n-Pr Cl 3-276 CH₂OCH₂CH₂OMe i-Pr Cl 3-277 CH₂OCH₂CH₂OEt Me Cl 3-278 CH₂OCH₂CH₂OEt Et Cl 3-279 CH₂OCH₂CH₂OEt n-Pr Cl 3-280 CH₂OCH₂CH₂OEt i-Pr Cl 3-281 CH₂OCH₂CH₂CH₂OMe Me Cl 3-282 CH₂OCH₂CH₂CH₂OMe Et Cl 3-283 CH₂OCH₂CH₂CH₂OMe n-Pr Cl 3-284 CH₂OCH₂CH₂CH₂OMe i-Pr Cl 3-285 CH₂OCH₂OMe Me Cl 3-286 CH₂OCH₂OMe Et Cl 3-287 CH₂OCH₂OMe n-Pr Cl 3-288 CH₂OCH₂OMe i-Pr Cl 3-289 CH₂OCH₂OEt Me Cl 3-290 CH₂OCH₂OEt Et Cl 3-291 CH₂OCH₂OEt n-Pr Cl 3-292 CH₂OCH₂OEt i-Pr Cl 3-293 CH₂OCH₂CH₂SO₂Me Me Cl 3-294 CH₂OCH₂CH₂SO₂Me Et Cl 3-295 CH₂OCH₂CH₂SO₂Me n-Pr Cl 3-296 CH₂OCH₂CH₂SO₂Me i-Pr Cl 3-297 CH₂SO₂CH₂CH₂OMe Me Cl 3-298 CH₂SO₂CH₂CH₂OMe Et Cl 3-299 CH₂SO₂CH₂CH₂OMe n-Pr Cl 3-300 CH₂SO₂CH₂CH₂OMe i-Pr Cl 3-301 CH₂SO₂CH₂CH₂SO₂Me Me Cl 3-302 CH₂SO₂CH₂CH₂SO₂Me Et Cl 3-303 CH₂SO₂CH₂CH₂SO₂Me n-Pr Cl 3-304 CH₂SO₂CH₂CH₂SO₂Me i-Pr Cl 3-305 Cl Me Br 3-306 Cl Et Br 3-307 Cl n-Pr Br 3-308 Cl i-Pr Br 3-309 Br Me Br 3-310 Br Et Br 3-311 Br n-Pr Br 3-312 Br i-Pr Br 3-313 Me Me Br 7.57 (d, 1H), 7.16 (d, 1H), 3.67 (s, 3H), 3.02 (s, 3H), 2.69 (s, 3H), 1.75 (s, 3H) 3-314 Me Et Br 3-315 Me n-Pr Br 3-316 Me i-Pr Br 3-317 Et Me Br 3-318 Et Et Br 3-319 Et n-Pr Br 3-320 Et i-Pr Br 3-321 CF₃ Me Br 3-322 CF₃ Et Br 3-323 CF₃ n-Pr Br 3-324 CF₃ i-Pr Br 3-325 OMe Me Br 3-326 OMe Et Br 3-327 OMe n-Pr Br 3-328 OMe i-Pr Br 3-329 OEt Me Br 3-330 OEt Et Br 3-331 OEt n-Pr Br 3-332 OEt i-Pr Br 3-333 NO₂ Me Br 3-334 NO₂ Et Br 3-335 NO₂ n-Pr Br 3-336 NO₂ i-Pr Br 3-337 SO₂Me Me Br 3-338 SO₂Me Et Br 3-339 SO₂Me n-Pr Br 3-340 SO₂Me i-Pr Br 3-341 CH₂OMe Me Br 3-342 CH₂OMe Et Br 3-343 CH₂OMe n-Pr Br 3-344 CH₂OMe i-Pr Br 3-345 CH₂SO₂Me Me Br 3-346 CH₂SO₂Me Et Br 3-347 CH₂SO₂Me n-Pr Br 3-348 CH₂SO₂Me i-Pr Br 3-349 CH₂OCH₂CH₂OMe Me Br 3-350 CH₂OCH₂CH₂OMe Et Br 3-351 CH₂OCH₂CH₂OMe n-Pr Br 3-352 CH₂OCH₂CH₂OMe i-Pr Br 3-353 CH₂OCH₂CH₂OEt Me Br 3-354 CH₂OCH₂CH₂OEt Et Br 3-355 CH₂OCH₂CH₂OEt n-Pr Br 3-356 CH₂OCH₂CH₂OEt i-Pr Br 3-357 CH₂OCH₂CH₂CH₂OMe Me Br 3-358 CH₂OCH₂CH₂CH₂OMe Et Br 3-359 CH₂OCH₂CH₂CH₂OMe n-Pr Br 3-360 CH₂OCH₂CH₂CH₂OMe i-Pr Br 3-361 CH₂OCH₂OMe Me Br 3-362 CH₂OCH₂OMe Et Br 3-363 CH₂OCH₂OMe n-Pr Br 3-364 CH₂OCH₂OMe i-Pr Br 3-365 CH₂OCH₂OEt Me Br 3-366 CH₂OCH₂OEt Et Br 3-367 CH₂OCH₂OEt n-Pr Br 3-368 CH₂OCH₂OEt i-Pr Br 3-369 CH₂OCH₂CH₂SO₂Me Me Br 3-370 CH₂OCH₂CH₂SO₂Me Et Br 3-371 CH₂OCH₂CH₂SO₂Me n-Pr Br 3-372 CH₂OCH₂CH₂SO₂Me i-Pr Br 3-373 CH₂SO₂CH₂CH₂OMe Me Br 3-374 CH₂SO₂CH₂CH₂OMe Et Br 3-375 CH₂SO₂CH₂CH₂OMe n-Pr Br 3-376 CH₂SO₂CH₂CH₂OMe i-Pr Br 3-377 CH₂SO₂CH₂CH₂SO₂Me Me Br 3-378 CH₂SO₂CH₂CH₂SO₂Me Et Br 3-379 CH₂SO₂CH₂CH₂SO₂Me n-Pr Br 3-380 CH₂SO₂CH₂CH₂SO₂Me i-Pr Br 3-381 Cl Me I 3-382 Cl Et I 3-383 Cl n-Pr I 3-384 Cl i-Pr I 3-385 Br Me I 3-386 Br Et I 3-387 Br n-Pr I 3-388 Br i-Pr I 3-389 Me Me I 7.68 (d, 1H), 6.96 (d, 1H), 3.65 (s, 3H), 2.96 (s, 3H), 2.68 (s, 3H), 1.74 (s, 3H) 3-390 Me Et I 3-391 Me n-Pr I 3-392 Me i-Pr I 3-393 Et Me I 3-394 Et Et I 3-395 Et n-Pr I 3-396 Et i-Pr I 3-397 CF₃ Me I 3-398 CF₃ Et I 3-399 CF₃ n-Pr I 3-400 CF₃ i-Pr I 3-401 OMe Me I 3-402 OMe Et I 3-403 OMe n-Pr I 3-404 OMe i-Pr I 3-405 OEt Me I 3-406 OEt Et I 3-407 OEt n-Pr I 3-408 OEt i-Pr I 3-409 NO₂ Me I 3-410 NO₂ Et I 3-411 NO₂ n-Pr I 3-412 NO₂ i-Pr I 3-413 SO₂Me Me I 3-414 SO₂Me Et I 3-415 SO₂Me n-Pr I 3-416 SO₂Me i-Pr I 3-417 CH₂OMe Me I 3-418 CH₂OMe Et I 3-419 CH₂OMe n-Pr I 3-420 CH₂OMe i-Pr I 3-421 CH₂SO₂Me Me I 3-422 CH₂SO₂Me Et I 3-423 CH₂SO₂Me n-Pr I 3-424 CH₂SO₂Me i-Pr I 3-425 CH₂OCH₂CH₂OMe Me I 3-426 CH₂OCH₂CH₂OMe Et I 3-427 CH₂OCH₂CH₂OMe n-Pr I 3-428 CH₂OCH₂CH₂OMe i-Pr I 3-429 CH₂OCH₂CH₂OEt Me I 3-430 CH₂OCH₂CH₂OEt Et I 3-431 CH₂OCH₂CH₂OEt n-Pr I 3-432 CH₂OCH₂CH₂OEt i-Pr I 3-433 CH₂OCH₂CH₂CH₂OMe Me I 3-434 CH₂OCH₂CH₂CH₂OMe Et I 3-435 CH₂OCH₂CH₂CH₂OMe n-Pr I 3-436 CH₂OCH₂CH₂CH₂OMe i-Pr I 3-437 CH₂OCH₂OMe Me I 3-438 CH₂OCH₂OMe Et I 3-439 CH₂OCH₂OMe n-Pr I 3-440 CH₂OCH₂OMe i-Pr I 3-441 CH₂OCH₂OEt Me I 3-442 CH₂OCH₂OEt Et I 3-443 CH₂OCH₂OEt n-Pr I 3-444 CH₂OCH₂OEt i-Pr I 3-445 CH₂OCH₂CH₂SO₂Me Me I 3-446 CH₂OCH₂CH₂SO₂Me Et I 3-447 CH₂OCH₂CH₂SO₂Me n-Pr I 3-448 CH₂OCH₂CH₂SO₂Me i-Pr I 3-449 CH₂SO₂CH₂CH₂OMe Me I 3-450 CH₂SO₂CH₂CH₂OMe Et I 3-451 CH₂SO₂CH₂CH₂OMe n-Pr I 3-452 CH₂SO₂CH₂CH₂OMe i-Pr I 3-453 CH₂SO₂CH₂CH₂SO₂Me Me I 3-454 CH₂SO₂CH₂CH₂SO₂Me Et I 3-455 CH₂SO₂CH₂CH₂SO₂Me n-Pr I 3-456 CH₂SO₂CH₂CH₂SO₂Me i-Pr I 3-457 Cl Me NO₂ 3-458 Cl Et NO₂ 3-459 Cl n-Pr NO₂ 3-460 Cl i-Pr NO₂ 3-461 Br Me NO₂ 3-462 Br Et NO₂ 3-463 Br n-Pr NO₂ 3-464 Br i-Pr NO₂ 3-465 Me Me NO₂ 3-466 Me Et NO₂ 3-467 Me n-Pr NO₂ 3-468 Me i-Pr NO₂ 3-469 Et Me NO₂ 3-470 Et Et NO₂ 3-471 Et n-Pr NO₂ 3-472 Et i-Pr NO₂ 3-473 CF₃ Me NO₂ 3-474 CF₃ Et NO₂ 3-475 CF₃ n-Pr NO₂ 3-476 CF₃ i-Pr NO₂ 3-477 OMe Me NO₂ 3-478 OMe Et NO₂ 3-479 OMe n-Pr NO₂ 3-480 OMe i-Pr NO₂ 3-481 OEt Me NO₂ 3-482 OEt Et NO₂ 3-483 OEt n-Pr NO₂ 3-484 OEt i-Pr NO₂ 3-485 NO₂ Me NO₂ 3-486 NO₂ Et NO₂ 3-487 NO₂ n-Pr NO₂ 3-488 NO₂ i-Pr NO₂ 3-489 SO₂Me Me NO₂ 3-490 SO₂Me Et NO₂ 3-491 SO₂Me n-Pr NO₂ 3-492 SO₂Me i-Pr NO₂ 3-493 CH₂OMe Me NO₂ 3-494 CH₂OMe Et NO₂ 3-495 CH₂OMe n-Pr NO₂ 3-496 CH₂OMe i-Pr NO₂ 3-497 CH₂SO₂Me Me NO₂ 3-498 CH₂SO₂Me Et NO₂ 3-499 CH₂SO₂Me n-Pr NO₂ 3-500 CH₂SO₂Me i-Pr NO₂ 3-501 CH₂OCH₂CH₂OMe Me NO₂ 3-502 CH₂OCH₂CH₂OMe Et NO₂ 3-503 CH₂OCH₂CH₂OMe n-Pr NO₂ 3-504 CH₂OCH₂CH₂OMe i-Pr NO₂ 3-505 CH₂OCH₂CH₂OEt Me NO₂ 3-506 CH₂OCH₂CH₂OEt Et NO₂ 3-507 CH₂OCH₂CH₂OEt n-Pr NO₂ 3-508 CH₂OCH₂CH₂OEt i-Pr NO₂ 3-509 CH₂OCH₂CH₂CH₂OMe Me NO₂ 3-510 CH₂OCH₂CH₂CH₂OMe Et NO₂ 3-511 CH₂OCH₂CH₂CH₂OMe n-Pr NO₂ 3-512 CH₂OCH₂CH₂CH₂OMe i-Pr NO₂ 3-513 CH₂OCH₂OMe Me NO₂ 3-514 CH₂OCH₂OMe Et NO₂ 3-515 CH₂OCH₂OMe n-Pr NO₂ 3-516 CH₂OCH₂OMe i-Pr NO₂ 3-517 CH₂OCH₂OEt Me NO₂ 3-518 CH₂OCH₂OEt Et NO₂ 3-519 CH₂OCH₂OEt n-Pr NO₂ 3-520 CH₂OCH₂OEt i-Pr NO₂ 3-521 CH₂OCH₂CH₂SO₂Me Me NO₂ 3-522 CH₂OCH₂CH₂SO₂Me Et NO₂ 3-523 CH₂OCH₂CH₂SO₂Me n-Pr NO₂ 3-524 CH₂OCH₂CH₂SO₂Me i-Pr NO₂ 3-525 CH₂SO₂CH₂CH₂OMe Me NO₂ 3-526 CH₂SO₂CH₂CH₂OMe Et NO₂ 3-527 CH₂SO₂CH₂CH₂OMe n-Pr NO₂ 3-528 CH₂SO₂CH₂CH₂OMe i-Pr NO₂ 3-529 CH₂SO₂CH₂CH₂SO₂Me Me NO₂ 3-530 CH₂SO₂CH₂CH₂SO₂Me Et NO₂ 3-531 CH₂SO₂CH₂CH₂SO₂Me n-Pr NO₂ 3-532 CH₂SO₂CH₂CH₂SO₂Me i-Pr NO₂

TABLE 4 Compounds of the formula (II) according to the invention (II)

Physical data: No. X R³ Y ¹H-NMR: δ [CDCl₃] 4-1  Cl Me SO₂Me 4-2  Cl Et SO₂Me 4-3  Cl n-Pr SO₂Me 4-4  Cl i-Pr SO₂Me 4-5  Br Me SO₂Me 4-6  Br Et SO₂Me 4-7  Br n-Pr SO₂Me 4-8  Br i-Pr SO₂Me 4-9  Me Me SO₂Me (DMSO-d₆): 7.93 (s, 2H), 3.46 (s, 3H), 3.08 (s, 3H), 2.87 (s, 3H) 4-10  Me Et SO₂Me (DMSO-d₆): 7.93 (s, 2H), 3.47 (m, 1H), 3.46 (s, 3H), 3.08 (m, 1H), 2.82 (s, 3H), 1.33 (t, 3H) 4-11  Me n-Pr SO₂Me 4-12  Me i-Pr SO₂Me 4-13  Et Me SO₂Me 4-14  Et Et SO₂Me 4-15  Et n-Pr SO₂Me 4-16  Et i-Pr SO₂Me 4-17  CF₃ Me SO₂Me 4-18  CF₃ Et SO₂Me 4-19  CF₃ n-Pr SO₂Me 4-20  CF₃ i-Pr SO₂Me 4-21  OMe Me SO₂Me 4-22  OMe Et SO₂Me 4-23  OMe n-Pr SO₂Me 4-24  OMe i-Pr SO₂Me 4-25  OEt Me SO₂Me 4-26  OEt Et SO₂Me 4-27  OEt n-Pr SO₂Me 4-28  OEt i-Pr SO₂Me 4-29  NO₂ Me SO₂Me 4-30  NO₂ Et SO₂Me 4-31  NO₂ n-Pr SO₂Me 4-32  NO₂ i-Pr SO₂Me 4-33  SO₂Me Me SO₂Me 4-34  SO₂Me Et SO₂Me 4-35  SO₂Me n-Pr SO₂Me 4-36  SO₂Me i-Pr SO₂Me 4-37  CH₂OMe Me SO₂Me 4-38  CH₂OMe Et SO₂Me 4-39  CH₂OMe n-Pr SO₂Me 4-40  CH₂OMe i-Pr SO₂Me 4-41  CH₂SO₂Me Me SO₂Me 4-42  CH₂SO₂Me Et SO₂Me 4-43  CH₂SO₂Me n-Pr SO₂Me 4-44  CH₂SO₂Me i-Pr SO₂Me 4-45  CH₂OCH₂CH₂OMe Me SO₂Me 4-46  CH₂OCH₂CH₂OMe Et SO₂Me 4-47  CH₂OCH₂CH₂OMe n-Pr SO₂Me 4-48  CH₂OCH₂CH₂OMe i-Pr SO₂Me 4-49  CH₂OCH₂CH₂OEt Me SO₂Me 4-50  CH₂OCH₂CH₂OEt Et SO₂Me 4-51  CH₂OCH₂CH₂OEt n-Pr SO₂Me 4-52  CH₂OCH₂CH₂OEt i-Pr SO₂Me 4-53  CH₂OCH₂CH₂CH₂OMe Me SO₂Me 4-54  CH₂OCH₂CH₂CH₂OMe Et SO₂Me 4-55  CH₂OCH₂CH₂CH₂OMe n-Pr SO₂Me 4-56  CH₂OCH₂CH₂CH₂OMe i-Pr SO₂Me 4-57  CH₂OCH₂OMe Me SO₂Me 4-58  CH₂OCH₂OMe Et SO₂Me 4-59  CH₂OCH₂OMe n-Pr SO₂Me 4-60  CH₂OCH₂OMe i-Pr SO₂Me 4-61  CH₂OCH₂OEt Me SO₂Me 4-62  CH₂OCH₂OEt Et SO₂Me 4-63  CH₂OCH₂OEt n-Pr SO₂Me 4-64  CH₂OCH₂OEt i-Pr SO₂Me 4-65  CH₂OCH₂CH₂SO₂Me Me SO₂Me 4-66  CH₂OCH₂CH₂SO₂Me Et SO₂Me 4-67  CH₂OCH₂CH₂SO₂Me n-Pr SO₂Me 4-68  CH₂OCH₂CH₂SO₂Me i-Pr SO₂Me 4-69  CH₂SO₂CH₂CH₂OMe Me SO₂Me 4-70  CH₂SO₂CH₂CH₂OMe Et SO₂Me 4-71  CH₂SO₂CH₂CH₂OMe n-Pr SO₂Me 4-72  CH₂SO₂CH₂CH₂OMe i-Pr SO₂Me 4-73  CH₂SO₂CH₂CH₂SO₂Me Me SO₂Me 4-74  CH₂SO₂CH₂CH₂SO₂Me Et SO₂Me 4-75  CH₂SO₂CH₂CH₂SO₂Me n-Pr SO₂Me 4-76  CH₂SO₂CH₂CH₂SO₂Me i-Pr SO₂Me 4-77  Cl Me SO₂Et 4-78  Cl Et SO₂Et 4-79  Cl n-Pr SO₂Et 4-80  Cl i-Pr SO₂Et 4-81  Br Me SO₂Et 4-82  Br Et SO₂Et 4-83  Br n-Pr SO₂Et 4-84  Br i-Pr SO₂Et 4-85  Me Me SO₂Et 4-86  Me Et SO₂Et 4-87  Me n-Pr SO₂Et 4-88  Me i-Pr SO₂Et 4-89  Et Me SO₂Et 4-90  Et Et SO₂Et 4-91  Et n-Pr SO₂Et 4-92  Et i-Pr SO₂Et 4-93  CF₃ Me SO₂Et 4-94  CF₃ Et SO₂Et 4-95  CF₃ n-Pr SO₂Et 4-96  CF₃ i-Pr SO₂Et 4-97  OMe Me SO₂Et 4-98  OMe Et SO₂Et 4-99  OMe n-Pr SO₂Et 4-100 OMe i-Pr SO₂Et 4-101 OEt Me SO₂Et 4-102 OEt Et SO₂Et 4-103 OEt n-Pr SO₂Et 4-104 OEt i-Pr SO₂Et 4-105 NO₂ Me SO₂Et 4-106 NO₂ Et SO₂Et 4-107 NO₂ n-Pr SO₂Et 4-108 NO₂ i-Pr SO₂Et 4-109 SO₂Me Me SO₂Et 4-110 SO₂Me Et SO₂Et 4-111 SO₂Me n-Pr SO₂Et 4-112 SO₂Me i-Pr SO₂Et 4-113 CH₂OMe Me SO₂Et 4-114 CH₂OMe Et SO₂Et 4-115 CH₂OMe n-Pr SO₂Et 4-116 CH₂OMe i-Pr SO₂Et 4-117 CH₂SO₂Me Me SO₂Et 4-118 CH₂SO₂Me Et SO₂Et 4-119 CH₂SO₂Me n-Pr SO₂Et 4-120 CH₂SO₂Me i-Pr SO₂Et 4-121 CH₂OCH₂CH₂OMe Me SO₂Et 4-122 CH₂OCH₂CH₂OMe Et SO₂Et 4-123 CH₂OCH₂CH₂OMe n-Pr SO₂Et 4-124 CH₂OCH₂CH₂OMe i-Pr SO₂Et 4-125 CH₂OCH₂CH₂OEt Me SO₂Et 4-126 CH₂OCH₂CH₂OEt Et SO₂Et 4-127 CH₂OCH₂CH₂OEt n-Pr SO₂Et 4-128 CH₂OCH₂CH₂OEt i-Pr SO₂Et 4-129 CH₂OCH₂CH₂CH₂OMe Me SO₂Et 4-130 CH₂OCH₂CH₂CH₂OMe Et SO₂Et 4-131 CH₂OCH₂CH₂CH₂OMe n-Pr SO₂Et 4-132 CH₂OCH₂CH₂CH₂OMe i-Pr SO₂Et 4-133 CH₂OCH₂OMe Me SO₂Et 4-134 CH₂OCH₂OMe Et SO₂Et 4-135 CH₂OCH₂OMe n-Pr SO₂Et 4-136 CH₂OCH₂OMe i-Pr SO₂Et 4-137 CH₂OCH₂OEt Me SO₂Et 4-138 CH₂OCH₂OEt Et SO₂Et 4-139 CH₂OCH₂OEt n-Pr SO₂Et 4-140 CH₂OCH₂OEt i-Pr SO₂Et 4-141 CH₂OCH₂CH₂SO₂Me Me SO₂Et 4-142 CH₂OCH₂CH₂SO₂Me Et SO₂Et 4-143 CH₂OCH₂CH₂SO₂Me n-Pr SO₂Et 4-144 CH₂OCH₂CH₂SO₂Me i-Pr SO₂Et 4-145 CH₂SO₂CH₂CH₂OMe Me SO₂Et 4-146 CH₂SO₂CH₂CH₂OMe Et SO₂Et 4-147 CH₂SO₂CH₂CH₂OMe n-Pr SO₂Et 4-148 CH₂SO₂CH₂CH₂OMe i-Pr SO₂Et 4-149 CH₂SO₂CH₂CH₂SO₂Me Me SO₂Et 4-150 CH₂SO₂CH₂CH₂SO₂Me Et SO₂Et 4-151 CH₂SO₂CH₂CH₂SO₂Me n-Pr SO₂Et 4-152 CH₂SO₂CH₂CH₂SO₂Me i-Pr SO₂Et 4-153 Cl Me F 4-154 Cl Et F 4-155 Cl n-Pr F 4-156 Cl i-Pr F 4-157 Br Me F 4-158 Br Et F 4-159 Br n-Pr F 4-160 Br i-Pr F 4-161 Me Me F 4-162 Me Et F 4-163 Me n-Pr F 4-164 Me i-Pr F 4-165 Et Me F 4-166 Et Et F 4-167 Et n-Pr F 4-168 Et i-Pr F 4-169 CF₃ Me F 4-170 CF₃ Et F 4-171 CF₃ n-Pr F 4-172 CF₃ i-Pr F 4-173 OMe Me F 4-174 OMe Et F 4-175 OMe n-Pr F 4-176 OMe i-Pr F 4-177 OEt Me F 4-178 OEt Et F 4-179 OEt n-Pr F 4-180 OEt i-Pr F 4-181 NO₂ Me F 4-182 NO₂ Et F 4-183 NO₂ n-Pr F 4-184 NO₂ i-Pr F 4-185 SO₂Me Me F 4-186 SO₂Me Et F 4-187 SO₂Me n-Pr F 4-188 SO₂Me i-Pr F 4-189 CH₂OMe Me F 4-190 CH₂OMe Et F 4-191 CH₂OMe n-Pr F 4-192 CH₂OMe i-Pr F 4-193 CH₂SO₂Me Me F 4-194 CH₂SO₂Me Et F 4-195 CH₂SO₂Me n-Pr F 4-196 CH₂SO₂Me i-Pr F 4-197 CH₂OCH₂CH₂OMe Me F 4-198 CH₂OCH₂CH₂OMe Et F 4-199 CH₂OCH₂CH₂OMe n-Pr F 4-200 CH₂OCH₂CH₂OMe i-Pr F 4-201 CH₂OCH₂CH₂OEt Me F 4-202 CH₂OCH₂CH₂OEt Et F 4-203 CH₂OCH₂CH₂OEt n-Pr F 4-204 CH₂OCH₂CH₂OEt i-Pr F 4-205 CH₂OCH₂CH₂CH₂OMe Me F 4-206 CH₂OCH₂CH₂CH₂OMe Et F 4-207 CH₂OCH₂CH₂CH₂OMe n-Pr F 4-208 CH₂OCH₂CH₂CH₂OMe i-Pr F 4-209 CH₂OCH₂OMe Me F 4-210 CH₂OCH₂OMe Et F 4-211 CH₂OCH₂OMe n-Pr F 4-212 CH₂OCH₂OMe i-Pr F 4-213 CH₂OCH₂OEt Me F 4-214 CH₂OCH₂OEt Et F 4-215 CH₂OCH₂OEt n-Pr F 4-216 CH₂OCH₂OEt i-Pr F 4-217 CH₂OCH₂CH₂SO₂Me Me F 4-218 CH₂OCH₂CH₂SO₂Me Et F 4-219 CH₂OCH₂CH₂SO₂Me n-Pr F 4-220 CH₂OCH₂CH₂SO₂Me i-Pr F 4-221 CH₂SO₂CH₂CH₂OMe Me F 4-222 CH₂SO₂CH₂CH₂OMe Et F 4-223 CH₂SO₂CH₂CH₂OMe n-Pr F 4-224 CH₂SO₂CH₂CH₂OMe i-Pr F 4-225 CH₂SO₂CH₂CH₂SO₂Me Me F 4-226 CH₂SO₂CH₂CH₂SO₂Me Et F 4-227 CH₂SO₂CH₂CH₂SO₂Me n-Pr F 4-228 CH₂SO₂CH₂CH₂SO₂Me i-Pr F 4-229 Cl Me Cl 4-230 Cl Et Cl 4-231 Cl n-Pr Cl 4-232 Cl i-Pr Cl 4-233 Br Me Cl 4-234 Br Et Cl 4-235 Br n-Pr Cl 4-236 Br i-Pr Cl 4-237 Me Me Cl (DMSO-d₆): 7.77 (d, 1H), 7.47 (d, 1H), 3.01 (s, 3H), 2.78 (s, 3H) 4-238 Me Et Cl 7.92 (d, 1H), 7.35 (d, 1H), 3.39 (m, 1H), 3.16 (m, 1H), 2.92 (s, 3H), 1.38 (t, 3H) 4-239 Me n-Pr Cl 4-240 Me i-Pr Cl 4-241 Et Me Cl 4-242 Et Et Cl 4-243 Et n-Pr Cl 4-244 Et i-Pr Cl 4-245 CF₃ Me Cl 4-246 CF₃ Et Cl 4-247 CF₃ n-Pr Cl 4-248 CF₃ i-Pr Cl 4-249 OMe Me Cl 4-250 OMe Et Cl 4-251 OMe n-Pr Cl 4-252 OMe i-Pr Cl 4-253 OEt Me Cl 4-254 OEt Et Cl 4-255 OEt n-Pr Cl 4-256 OEt i-Pr Cl 4-257 NO₂ Me Cl 4-258 NO₂ Et Cl 4-259 NO₂ n-Pr Cl 4-260 NO₂ i-Pr Cl 4-261 SO₂Me Me Cl 4-262 SO₂Me Et Cl 4-263 SO₂Me n-Pr Cl 4-264 SO₂Me i-Pr Cl 4-265 CH₂OMe Me Cl 4-266 CH₂OMe Et Cl 4-267 CH₂OMe n-Pr Cl 4-268 CH₂OMe i-Pr Cl 4-269 CH₂SO₂Me Me Cl 4-270 CH₂SO₂Me Et Cl 4-271 CH₂SO₂Me n-Pr Cl 4-272 CH₂SO₂Me i-Pr Cl 4-273 CH₂OCH₂CH₂OMe Me Cl 4-274 CH₂OCH₂CH₂OMe Et Cl 4-275 CH₂OCH₂CH₂OMe n-Pr Cl 4-276 CH₂OCH₂CH₂OMe i-Pr Cl 4-277 CH₂OCH₂CH₂OEt Me Cl 4-278 CH₂OCH₂CH₂OEt Et Cl 4-279 CH₂OCH₂CH₂OEt n-Pr Cl 4-280 CH₂OCH₂CH₂OEt i-Pr Cl 4-281 CH₂OCH₂CH₂CH₂OMe Me Cl 4-282 CH₂OCH₂CH₂CH₂OMe Et Cl 4-283 CH₂OCH₂CH₂CH₂OMe n-Pr Cl 4-284 CH₂OCH₂CH₂CH₂OMe i-Pr Cl 4-285 CH₂OCH₂OMe Me Cl 4-286 CH₂OCH₂OMe Et Cl 4-287 CH₂OCH₂OMe n-Pr Cl 4-288 CH₂OCH₂OMe i-Pr Cl 4-289 CH₂OCH₂OEt Me Cl 4-290 CH₂OCH₂OEt Et Cl 4-291 CH₂OCH₂OEt n-Pr Cl 4-292 CH₂OCH₂OEt i-Pr Cl 4-293 CH₂OCH₂CH₂SO₂Me Me Cl 4-294 CH₂OCH₂CH₂SO₂Me Et Cl 4-295 CH₂OCH₂CH₂SO₂Me n-Pr Cl 4-296 CH₂OCH₂CH₂SO₂Me i-Pr Cl 4-297 CH₂SO₂CH₂CH₂OMe Me Cl 4-298 CH₂SO₂CH₂CH₂OMe Et Cl 4-299 CH₂SO₂CH₂CH₂OMe n-Pr Cl 4-300 CH₂SO₂CH₂CH₂OMe i-Pr Cl 4-301 CH₂SO₂CH₂CH₂SO₂Me Me Cl 4-302 CH₂SO₂CH₂CH₂SO₂Me Et Cl 4-303 CH₂SO₂CH₂CH₂SO₂Me n-Pr Cl 4-304 CH₂SO₂CH₂CH₂SO₂Me i-Pr Cl 4-305 Cl Me Br 4-306 Cl Et Br 4-307 Cl n-Pr Br 4-308 Cl i-Pr Br 4-309 Br Me Br 4-310 Br Et Br 4-311 Br n-Pr Br 4-312 Br i-Pr Br 4-313 Me Me Br (DMSO-d₆): 7.66 (d, 1H), 7.64 (d, 1H), 2.99 (s, 3H), 2.80 (s, 3H) 4-314 Me Et Br 4-315 Me n-Pr Br 4-316 Me i-Pr Br 4-317 Et Me Br 4-318 Et Et Br 4-319 Et n-Pr Br 4-320 Et i-Pr Br 4-321 CF₃ Me Br 4-322 CF₃ Et Br 4-323 CF₃ n-Pr Br 4-324 CF₃ i-Pr Br 4-325 OMe Me Br 4-326 OMe Et Br 4-327 OMe n-Pr Br 4-328 OMe i-Pr Br 4-329 OEt Me Br 4-330 OEt Et Br 4-331 OEt n-Pr Br 4-332 OEt i-Pr Br 4-333 NO₂ Me Br 4-334 NO₂ Et Br 4-335 NO₂ n-Pr Br 4-336 NO₂ i-Pr Br 4-337 SO₂Me Me Br 4-338 SO₂Me Et Br 4-339 SO₂Me n-Pr Br 4-340 SO₂Me i-Pr Br 4-341 CH₂OMe Me Br 4-342 CH₂OMe Et Br 4-343 CH₂OMe n-Pr Br 4-344 CH₂OMe i-Pr Br 4-345 CH₂SO₂Me Me Br 4-346 CH₂SO₂Me Et Br 4-347 CH₂SO₂Me n-Pr Br 4-348 CH₂SO₂Me i-Pr Br 4-349 CH₂OCH₂CH₂OMe Me Br 4-350 CH₂OCH₂CH₂OMe Et Br 4-351 CH₂OCH₂CH₂OMe n-Pr Br 4-352 CH₂OCH₂CH₂OMe i-Pr Br 4-353 CH₂OCH₂CH₂OEt Me Br 4-354 CH₂OCH₂CH₂OEt Et Br 4-355 CH₂OCH₂CH₂OEt n-Pr Br 4-356 CH₂OCH₂CH₂OEt i-Pr Br 4-357 CH₂OCH₂CH₂CH₂OMe Me Br 4-358 CH₂OCH₂CH₂CH₂OMe Et Br 4-359 CH₂OCH₂CH₂CH₂OMe n-Pr Br 4-360 CH₂OCH₂CH₂CH₂OMe i-Pr Br 4-361 CH₂OCH₂OMe Me Br 4-362 CH₂OCH₂OMe Et Br 4-363 CH₂OCH₂OMe n-Pr Br 4-364 CH₂OCH₂OMe i-Pr Br 4-365 CH₂OCH₂OEt Me Br 4-366 CH₂OCH₂OEt Et Br 4-367 CH₂OCH₂OEt n-Pr Br 4-368 CH₂OCH₂OEt i-Pr Br 4-369 CH₂OCH₂CH₂SO₂Me Me Br 4-370 CH₂OCH₂CH₂SO₂Me Et Br 4-371 CH₂OCH₂CH₂SO₂Me n-Pr Br 4-372 CH₂OCH₂CH₂SO₂Me i-Pr Br 4-373 CH₂SO₂CH₂CH₂OMe Me Br 4-374 CH₂SO₂CH₂CH₂OMe Et Br 4-375 CH₂SO₂CH₂CH₂OMe n-Pr Br 4-376 CH₂SO₂CH₂CH₂OMe i-Pr Br 4-377 CH₂SO₂CH₂CH₂SO₂Me Me Br 4-378 CH₂SO₂CH₂CH₂SO₂Me Et Br 4-379 CH₂SO₂CH₂CH₂SO₂Me n-Pr Br 4-380 CH₂SO₂CH₂CH₂SO₂Me i-Pr Br 4-381 Cl Me I 4-382 Cl Et I 4-383 Cl n-Pr I 4-384 Cl i-Pr I 4-385 Br Me I 4-386 Br Et I 4-387 Br n-Pr I 4-388 Br i-Pr I 4-389 Me Me I 7.87 (d, 1H), 7.61 (d, 1H), 2.99 (s, 3H), 2.98 (s, 3H) 4-390 Me Et I 4-391 Me n-Pr I 4-392 Me i-Pr I 4-393 Et Me I 4-394 Et Et I 4-395 Et n-Pr I 4-396 Et i-Pr I 4-397 CF₃ Me I 4-398 CF₃ Et I 4-399 CF₃ n-Pr I 4-400 CF₃ i-Pr I 4-401 OMe Me I 4-402 OMe Et I 4-403 OMe n-Pr I 4-404 OMe i-Pr I 4-405 OEt Me I 4-406 OEt Et I 4-407 OEt n-Pr I 4-408 OEt i-Pr I 4-409 NO₂ Me I 4-410 NO₂ Et I 4-411 NO₂ n-Pr I 4-412 NO₂ i-Pr I 4-413 SO₂Me Me I 4-414 SO₂Me Et I 4-415 SO₂Me n-Pr I 4-416 SO₂Me i-Pr I 4-417 CH₂OMe Me I 4-418 CH₂OMe Et I 4-419 CH₂OMe n-Pr I 4-420 CH₂OMe i-Pr I 4-421 CH₂SO₂Me Me I 4-422 CH₂SO₂Me Et I 4-423 CH₂SO₂Me n-Pr I 4-424 CH₂SO₂Me i-Pr I 4-425 CH₂OCH₂CH₂OMe Me I 4-426 CH₂OCH₂CH₂OMe Et I 4-427 CH₂OCH₂CH₂OMe n-Pr I 4-428 CH₂OCH₂CH₂OMe i-Pr I 4-429 CH₂OCH₂CH₂OEt Me I 4-430 CH₂OCH₂CH₂OEt Et I 4-431 CH₂OCH₂CH₂OEt n-Pr I 4-432 CH₂OCH₂CH₂OEt i-Pr I 4-433 CH₂OCH₂CH₂CH₂OMe Me I 4-434 CH₂OCH₂CH₂CH₂OMe Et I 4-435 CH₂OCH₂CH₂CH₂OMe n-Pr I 4-436 CH₂OCH₂CH₂CH₂OMe i-Pr I 4-437 CH₂OCH₂OMe Me I 4-438 CH₂OCH₂OMe Et I 4-439 CH₂OCH₂OMe n-Pr I 4-440 CH₂OCH₂OMe i-Pr I 4-441 CH₂OCH₂OEt Me I 4-442 CH₂OCH₂OEt Et I 4-443 CH₂OCH₂OEt n-Pr I 4-444 CH₂OCH₂OEt i-Pr I 4-445 CH₂OCH₂CH₂SO₂Me Me I 4-446 CH₂OCH₂CH₂SO₂Me Et I 4-447 CH₂OCH₂CH₂SO₂Me n-Pr I 4-448 CH₂OCH₂CH₂SO₂Me i-Pr I 4-449 CH₂SO₂CH₂CH₂OMe Me I 4-450 CH₂SO₂CH₂CH₂OMe Et I 4-451 CH₂SO₂CH₂CH₂OMe n-Pr I 4-452 CH₂SO₂CH₂CH₂OMe i-Pr I 4-453 CH₂SO₂CH₂CH₂SO₂Me Me I 4-454 CH₂SO₂CH₂CH₂SO₂Me Et I 4-455 CH₂SO₂CH₂CH₂SO₂Me n-Pr I 4-456 CH₂SO₂CH₂CH₂SO₂Me i-Pr I 4-457 Cl Me NO₂ 4-458 Cl Et NO₂ 4-459 Cl n-Pr NO₂ 4-460 Cl i-Pr NO₂ 4-461 Br Me NO₂ 4-462 Br Et NO₂ 4-463 Br n-Pr NO₂ 4-464 Br i-Pr NO₂ 4-465 Me Me NO₂ 4-466 Me Et NO₂ 4-467 Me n-Pr NO₂ 4-468 Me i-Pr NO₂ 4-469 Et Me NO₂ 4-470 Et Et NO₂ 4-471 Et n-Pr NO₂ 4-472 Et i-Pr NO₂ 4-473 CF₃ Me NO₂ 4-474 CF₃ Et NO₂ 4-475 CF₃ n-Pr NO₂ 4-476 CF₃ i-Pr NO₂ 4-477 OMe Me NO₂ 4-478 OMe Et NO₂ 4-479 OMe n-Pr NO₂ 4-480 OMe i-Pr NO₂ 4-481 OEt Me NO₂ 4-482 OEt Et NO₂ 4-483 OEt n-Pr NO₂ 4-484 OEt i-Pr NO₂ 4-485 NO₂ Me NO₂ 4-486 NO₂ Et NO₂ 4-487 NO₂ n-Pr NO₂ 4-488 NO₂ i-Pr NO₂ 4-489 SO₂Me Me NO₂ 4-490 SO₂Me Et NO₂ 4-491 SO₂Me n-Pr NO₂ 4-492 SO₂Me i-Pr NO₂ 4-493 CH₂OMe Me NO₂ 4-494 CH₂OMe Et NO₂ 4-495 CH₂OMe n-Pr NO₂ 4-496 CH₂OMe i-Pr NO₂ 4-497 CH₂SO₂Me Me NO₂ 4-498 CH₂SO₂Me Et NO₂ 4-499 CH₂SO₂Me n-Pr NO₂ 4-500 CH₂SO₂Me i-Pr NO₂ 4-501 CH₂OCH₂CH₂OMe Me NO₂ 4-502 CH₂OCH₂CH₂OMe Et NO₂ 4-503 CH₂OCH₂CH₂OMe n-Pr NO₂ 4-504 CH₂OCH₂CH₂OMe i-Pr NO₂ 4-505 CH₂OCH₂CH₂OEt Me NO₂ 4-506 CH₂OCH₂CH₂OEt Et NO₂ 4-507 CH₂OCH₂CH₂OEt n-Pr NO₂ 4-508 CH₂OCH₂CH₂OEt i-Pr NO₂ 4-509 CH₂OCH₂CH₂CH₂OMe Me NO₂ 4-510 CH₂OCH₂CH₂CH₂OMe Et NO₂ 4-511 CH₂OCH₂CH₂CH₂OMe n-Pr NO₂ 4-512 CH₂OCH₂CH₂CH₂OMe i-Pr NO₂ 4-513 CH₂OCH₂OMe Me NO₂ 4-514 CH₂OCH₂OMe Et NO₂ 4-515 CH₂OCH₂OMe n-Pr NO₂ 4-516 CH₂OCH₂OMe i-Pr NO₂ 4-517 CH₂OCH₂OEt Me NO₂ 4-518 CH₂OCH₂OEt Et NO₂ 4-519 CH₂OCH₂OEt n-Pr NO₂ 4-520 CH₂OCH₂OEt i-Pr NO₂ 4-521 CH₂OCH₂CH₂SO₂Me Me NO₂ 4-522 CH₂OCH₂CH₂SO₂Me Et NO₂ 4-523 CH₂OCH₂CH₂SO₂Me n-Pr NO₂ 4-524 CH₂OCH₂CH₂SO₂Me i-Pr NO₂ 4-525 CH₂SO₂CH₂CH₂OMe Me NO₂ 4-526 CH₂SO₂CH₂CH₂OMe Et NO₂ 4-527 CH₂SO₂CH₂CH₂OMe n-Pr NO₂ 4-528 CH₂SO₂CH₂CH₂OMe i-Pr NO₂ 4-529 CH₂SO₂CH₂CH₂SO₂Me Me NO₂ 4-530 CH₂SO₂CH₂CH₂SO₂Me Et NO₂ 4-531 CH₂SO₂CH₂CH₂SO₂Me n-Pr NO₂ 4-532 CH₂SO₂CH₂CH₂SO₂Me i-Pr NO₂

TABLE 5 Compounds of the formula (I) according to the invention in which R¹ is methyl and R² is hydrogen.

Physical data: No. X R³ Y R⁴ ¹H-NMR: δ [CDCl₃] 5-1  Cl Me SO₂Me —SO₂-n-Pr 5-2  Cl Et SO₂Me —SO₂-n-Pr 5-3  Me Me SO₂Me —SO₂-n-Pr 5-4  Me Et SO₂Me —SO₂-n-Pr 5-5  CF₃ Me SO₂Me —SO₂-n-Pr 5-6  CF₃ Et SO₂Me —SO₂-n-Pr 5-7  OMe Me SO₂Me —SO₂-n-Pr 5-8  OMe Et SO₂Me —SO₂-n-Pr 5-9  NO₂ Me SO₂Me —SO₂-n-Pr 5-10  NO₂ Et SO₂Me —SO₂-n-Pr 5-11  SO₂Me Me SO₂Me —SO₂-n-Pr 5-12  SO₂Me Et SO₂Me —SO₂-n-Pr 5-13  CH₂OMe Me SO₂Me —SO₂-n-Pr 5-14  CH₂OMe Et SO₂Me —SO₂-n-Pr 5-15  CH₂SO₂Me Me SO₂Me —SO₂-n-Pr 5-16  CH₂SO₂Me Et SO₂Me —SO₂-n-Pr 5-17  CH₂OCH₂CH₂OMe Me SO₂Me —SO₂-n-Pr 5-18  CH₂OCH₂CH₂OMe Et SO₂Me —SO₂-n-Pr 5-19  Cl Me Cl —SO₂-n-Pr 5-20  Cl Et Cl —SO₂-n-Pr 5-21  Me Me Cl —SO₂-n-Pr 5-22  Me Et Cl —SO₂-n-Pr 5-23  CF₃ Me Cl —SO₂-n-Pr 5-24  CF₃ Et Cl —SO₂-n-Pr 5-25  OMe Me Cl —SO₂-n-Pr 5-26  OMe Et Cl —SO₂-n-Pr 5-27  NO₂ Me Cl —SO₂-n-Pr 5-28  NO₂ Et Cl —SO₂-n-Pr 5-29  SO₂Me Me Cl —SO₂-n-Pr 5-30  SO₂Me Et Cl —SO₂-n-Pr 5-31  CH₂OMe Me Cl —SO₂-n-Pr 5-32  CH₂OMe Et Cl —SO₂-n-Pr 5-33  CH₂SO₂Me Me Cl —SO₂-n-Pr 5-34  CH₂SO₂Me Et Cl —SO₂-n-Pr 5-35  CH₂OCH₂CH₂OMe Me Cl —SO₂-n-Pr 5-36  CH₂OCH₂CH₂OMe Et Cl —SO₂-n-Pr 5-37  Cl Me Br —SO₂-n-Pr 5-38  Cl Et Br —SO₂-n-Pr 5-39  Me Me Br —SO₂-n-Pr 5-40  Me Et Br —SO₂-n-Pr 5-41  CF₃ Me Br —SO₂-n-Pr 5-42  CF₃ Et Br —SO₂-n-Pr 5-43  OMe Me Br —SO₂-n-Pr 5-44  OMe Et Br —SO₂-n-Pr 5-45  NO₂ Me Br —SO₂-n-Pr 5-46  NO₂ Et Br —SO₂-n-Pr 5-47  SO₂Me Me Br —SO₂-n-Pr 5-48  SO₂Me Et Br —SO₂-n-Pr 5-49  CH₂OMe Me Br —SO₂-n-Pr 5-50  CH₂OMe Et Br —SO₂-n-Pr 5-51  CH₂SO₂Me Me Br —SO₂-n-Pr 5-52  CH₂SO₂Me Et Br —SO₂-n-Pr 5-53  CH₂OCH₂CH₂OMe Me Br —SO₂-n-Pr 5-54  CH₂OCH₂CH₂OMe Et Br —SO₂-n-Pr 5-55  Cl Me I —SO₂-n-Pr 5-56  Cl Et I —SO₂-n-Pr 5-57  Me Me I —SO₂-n-Pr 5-58  Me Et I —SO₂-n-Pr 5-59  CF₃ Me I —SO₂-n-Pr 5-60  CF₃ Et I —SO₂-n-Pr 5-61  OMe Me I —SO₂-n-Pr 5-62  OMe Et I —SO₂-n-Pr 5-63  NO₂ Me I —SO₂-n-Pr 5-64  NO₂ Et I —SO₂-n-Pr 5-65  SO₂Me Me I —SO₂-n-Pr 5-66  SO₂Me Et I —SO₂-n-Pr 5-67  CH₂OMe Me I —SO₂-n-Pr 5-68  CH₂OMe Et I —SO₂-n-Pr 5-69  CH₂SO₂Me Me I —SO₂-n-Pr 5-70  CH₂SO₂Me Et I —SO₂-n-Pr 5-71  CH₂OCH₂CH₂OMe Me I —SO₂-n-Pr 5-72  CH₂OCH₂CH₂OMe Et I —SO₂-n-Pr 5-73  Cl Me NO₂ —SO₂-n-Pr 5-74  Cl Et NO₂ —SO₂-n-Pr 5-75  Me Me NO₂ —SO₂-n-Pr 5-76  Me Et NO₂ —SO₂-n-Pr 5-77  CF₃ Me NO₂ —SO₂-n-Pr 5-78  CF₃ Et NO₂ —SO₂-n-Pr 5-79  OMe Me NO₂ —SO₂-n-Pr 5-80  OMe Et NO₂ —SO₂-n-Pr 5-81  NO₂ Me NO₂ —SO₂-n-Pr 5-82  NO₂ Et NO₂ —SO₂-n-Pr 5-83  SO₂Me Me NO₂ —SO₂-n-Pr 5-84  SO₂Me Et NO₂ —SO₂-n-Pr 5-85  CH₂OMe Me NO₂ —SO₂-n-Pr 5-86  CH₂OMe Et NO₂ —SO₂-n-Pr 5-87  CH₂SO₂Me Me NO₂ —SO₂-n-Pr 5-88  CH₂SO₂Me Et NO₂ —SO₂-n-Pr 5-89  CH₂OCH₂CH₂OMe Me NO₂ —SO₂-n-Pr 5-90  CH₂OCH₂CH₂OMe Et NO₂ —SO₂-n-Pr 5-91  Cl Me SO₂Me —CO-Ph 5-92  Cl Et SO₂Me —CO-Ph 5-93  Me Me SO₂Me —CO-Ph 5-94  Me Et SO₂Me —CO-Ph 5-95  CF₃ Me SO₂Me —CO-Ph 5-96  CF₃ Et SO₂Me —CO-Ph 5-97  OMe Me SO₂Me —CO-Ph 5-98  OMe Et SO₂Me —CO-Ph 5-99  NO₂ Me SO₂Me —CO-Ph 5-100 NO₂ Et SO₂Me —CO-Ph 5-101 SO₂Me Me SO₂Me —CO-Ph 5-102 SO₂Me Et SO₂Me —CO-Ph 5-103 CH₂OMe Me SO₂Me —CO-Ph 5-104 CH₂OMe Et SO₂Me —CO-Ph 5-105 CH₂SO₂Me Me SO₂Me —CO-Ph 5-106 CH₂SO₂Me Et SO₂Me —CO-Ph 5-107 CH₂OCH₂CH₂OMe Me SO₂Me —CO-Ph 5-108 CH₂OCH₂CH₂OMe Et SO₂Me —CO-Ph 5-109 Cl Me Cl —CO-Ph 5-110 Cl Et Cl —CO-Ph 5-111 Me Me Cl —CO-Ph 5-112 Me Et Cl —CO-Ph 5-113 CF₃ Me Cl —CO-Ph 5-114 CF₃ Et Cl —CO-Ph 5-115 OMe Me Cl —CO-Ph 5-116 OMe Et Cl —CO-Ph 5-117 NO₂ Me Cl —CO-Ph 5-118 NO₂ Et Cl —CO-Ph 5-119 SO₂Me Me Cl —CO-Ph 5-120 SO₂Me Et Cl —CO-Ph 5-121 CH₂OMe Me Cl —CO-Ph 5-122 CH₂OMe Et Cl —CO-Ph 5-123 CH₂SO₂Me Me Cl —CO-Ph 5-124 CH₂SO₂Me Et Cl —CO-Ph 5-125 CH₂OCH₂CH₂OMe Me Cl —CO-Ph 5-126 CH₂OCH₂CH₂OMe Et Cl —CO-Ph 5-127 Cl Me Br —CO-Ph 5-128 Cl Et Br —CO-Ph 5-129 Me Me Br —CO-Ph 5-130 Me Et Br —CO-Ph 5-131 CF₃ Me Br —CO-Ph 5-132 CF₃ Et Br —CO-Ph 5-133 OMe Me Br —CO-Ph 5-134 OMe Et Br —CO-Ph 5-135 NO₂ Me Br —CO-Ph 5-136 NO₂ Et Br —CO-Ph 5-137 SO₂Me Me Br —CO-Ph 5-138 SO₂Me Et Br —CO-Ph 5-139 CH₂OMe Me Br —CO-Ph 5-140 CH₂OMe Et Br —CO-Ph 5-141 CH₂SO₂Me Me Br —CO-Ph 5-142 CH₂SO₂Me Et Br —CO-Ph 5-143 CH₂OCH₂CH₂OMe Me Br —CO-Ph 5-144 CH₂OCH₂CH₂OMe Et Br —CO-Ph 5-145 Cl Me Cl —CO-Ph 5-146 Cl Et Cl —CO-Ph 5-147 Me Me Cl —CO-Ph 5-148 Me Et Cl —CO-Ph 5-149 CF₃ Me Cl —CO-Ph 5-150 CF₃ Et Cl —CO-Ph 5-151 OMe Me Cl —CO-Ph 5-152 OMe Et Cl —CO-Ph 5-153 NO₂ Me Cl —CO-Ph 5-154 NO₂ Et Cl —CO-Ph 5-155 SO₂Me Me Cl —CO-Ph 5-156 SO₂Me Et Cl —CO-Ph 5-157 CH₂OMe Me Cl —CO-Ph 5-158 CH₂OMe Et Cl —CO-Ph 5-159 CH₂SO₂Me Me Cl —CO-Ph 5-160 CH₂SO₂Me Et Cl —CO-Ph 5-161 CH₂OCH₂CH₂OMe Me Cl —CO-Ph 5-162 CH₂OCH₂CH₂OMe Et Cl —CO-Ph 5-163 Cl Me NO₂ —CO-Ph 5-164 Cl Et NO₂ —CO-Ph 5-165 Me Me NO₂ —CO-Ph 5-166 Me Et NO₂ —CO-Ph 5-167 CF₃ Me NO₂ —CO-Ph 5-168 CF₃ Et NO₂ —CO-Ph 5-169 OMe Me NO₂ —CO-Ph 5-170 OMe Et NO₂ —CO-Ph 5-171 NO₂ Me NO₂ —CO-Ph 5-172 NO₂ Et NO₂ —CO-Ph 5-173 SO₂Me Me NO₂ —CO-Ph 5-174 SO₂Me Et NO₂ —CO-Ph 5-175 CH₂OMe Me NO₂ —CO-Ph 5-176 CH₂OMe Et NO₂ —CO-Ph 5-177 CH₂SO₂Me Me NO₂ —CO-Ph 5-178 CH₂SO₂Me Et NO₂ —CO-Ph 5-179 CH₂OCH₂CH₂OMe Me NO₂ —CO-Ph 5-180 CH₂OCH₂CH₂OMe Et NO₂ —CO-Ph 5-181 Cl Me SO₂Me —CH₂—CO— (4-Me-Ph) 5-182 Cl Et SO₂Me —CH₂—CO— (4-Me-Ph) 5-183 Me Me SO₂Me —CH₂—CO— (4-Me-Ph) 5-184 Me Et SO₂Me —CH₂—CO— (4-Me-Ph) 5-185 CF₃ Me SO₂Me —CH₂—CO— (4-Me-Ph) 5-186 CF₃ Et SO₂Me —CH₂—CO— (4-Me-Ph) 5-187 OMe Me SO₂Me —CH₂—CO— (4-Me-Ph) 5-188 OMe Et SO₂Me —CH₂—CO— (4-Me-Ph) 5-189 NO₂ Me SO₂Me —CH₂—CO— (4-Me-Ph) 5-190 NO₂ Et SO₂Me —CH₂—CO— (4-Me-Ph) 5-191 SO₂Me Me SO₂Me —CH₂—CO— (4-Me-Ph) 5-192 SO₂Me Et SO₂Me —CH₂—CO— (4-Me-Ph) 5-193 CH₂OMe Me SO₂Me —CH₂—CO— (4-Me-Ph) 5-194 CH₂OMe Et SO₂Me —CH₂—CO— (4-Me-Ph) 5-195 CH₂SO₂Me Me SO₂Me —CH₂—CO— (4-Me-Ph) 5-196 CH₂SO₂Me Et SO₂Me —CH₂—CO— (4-Me-Ph) 5-197 CH₂OCH₂CH₂OMe Me SO₂Me —CH₂—CO— (4-Me-Ph) 5-198 CH₂OCH₂CH₂OMe Et SO₂Me —CH₂—CO— (4-Me-Ph) 5-199 Cl Me Cl —CH₂—CO— (4-Me-Ph) 5-200 Cl Et Cl —CH₂—CO— (4-Me-Ph) 5-201 Me Me Cl —CH₂—CO— (4-Me-Ph) 5-202 Me Et Cl —CH₂—CO— (4-Me-Ph) 5-203 CF₃ Me Cl —CH₂—CO— (4-Me-Ph) 5-204 CF₃ Et Cl —CH₂—CO— (4-Me-Ph) 5-205 OMe Me Cl —CH₂—CO— (4-Me-Ph) 5-206 OMe Et Cl —CH₂—CO— (4-Me-Ph) 5-207 NO₂ Me Cl —CH₂—CO— (4-Me-Ph) 5-208 NO₂ Et Cl —CH₂—CO— (4-Me-Ph) 5-209 SO₂Me Me Cl —CH₂—CO— (4-Me-Ph) 5-210 SO₂Me Et Cl —CH₂—CO— (4-Me-Ph) 5-211 CH₂OMe Me Cl —CH₂—CO— (4-Me-Ph) 5-212 CH₂OMe Et Cl —CH₂—CO— (4-Me-Ph) 5-213 CH₂SO₂Me Me Cl —CH₂—CO— (4-Me-Ph) 5-214 CH₂SO₂Me Et Cl —CH₂—CO— (4-Me-Ph) 5-215 CH₂OCH₂CH₂OMe Me Cl —CH₂—CO— (4-Me-Ph) 5-216 CH₂OCH₂CH₂OMe Et Cl —CH₂—CO— (4-Me-Ph) 5-217 Cl Me Br —CH₂—CO— (4-Me-Ph) 5-218 Cl Et Br —CH₂—CO— (4-Me-Ph) 5-219 Me Me Br —CH₂—CO— (4-Me-Ph) 5-220 Me Et Br —CH₂—CO— (4-Me-Ph) 5-221 CF₃ Me Br —CH₂—CO— (4-Me-Ph) 5-222 CF₃ Et Br —CH₂—CO— (4-Me-Ph) 5-223 OMe Me Br —CH₂—CO— (4-Me-Ph) 5-224 OMe Et Br —CH₂—CO— (4-Me-Ph) 5-225 NO₂ Me Br —CH₂—CO— (4-Me-Ph) 5-226 NO₂ Et Br —CH₂—CO— (4-Me-Ph) 5-227 SO₂Me Me Br —CH₂—CO— (4-Me-Ph) 5-228 SO₂Me Et Br —CH₂—CO— (4-Me-Ph) 5-229 CH₂OMe Me Br —CH₂—CO— (4-Me-Ph) 5-230 CH₂OMe Et Br —CH₂—CO— (4-Me-Ph) 5-231 CH₂SO₂Me Me Br —CH₂—CO— (4-Me-Ph) 5-232 CH₂SO₂Me Et Br —CH₂—CO— (4-Me-Ph) 5-233 CH₂OCH₂OMe Me Br —CH₂—CO— (4-Me-Ph) 5-234 CH₂OCH₂OMe Et Br —CH₂—CO— (4-Me-Ph) 5-235 Cl Me I —CH₂—CO— (4-Me-Ph) 5-236 Cl Et I —CH₂—CO— (4-Me-Ph) 5-237 Me Me I —CH₂—CO— (4-Me-Ph) 5-238 Me Et I —CH₂—CO— (4-Me-Ph) 5-239 CF₃ Me I —CH₂—CO— (4-Me-Ph) 5-240 CF₃ Et I —CH₂—CO— (4-Me-Ph) 5-241 OMe Me I —CH₂—CO— (4-Me-Ph) 5-242 OMe Et I —CH₂—CO— (4-Me-Ph) 5-243 NO₂ Me I —CH₂—CO— (4-Me-Ph) 5-244 NO₂ Et I —CH₂—CO— (4-Me-Ph) 5-245 SO₂Me Me I —CH₂—CO— (4-Me-Ph) 5-246 SO₂Me Et I —CH₂—CO— (4-Me-Ph) 5-247 CH₂OMe Me I —CH₂—CO— (4-Me-Ph) 5-248 CH₂OMe Et I —CH₂—CO— (4-Me-Ph) 5-249 CH₂SO₂Me Me I —CH₂—CO— (4-Me-Ph) 5-250 CH₂SO₂Me Et I —CH₂—CO— (4-Me-Ph) 5-251 CH₂OCH₂OMe Me I —CH₂—CO— (4-Me-Ph) 5-252 CH₂OCH₂OMe Et I —CH₂—CO— (4-Me-Ph) 5-253 Cl Me NO₂ —CH₂—CO— (4-Me-Ph) 5-254 Cl Et NO₂ —CH₂—CO— (4-Me-Ph) 5-255 Me Me NO₂ —CH₂—CO— (4-Me-Ph) 5-256 Me Et NO₂ —CH₂—CO— (4-Me-Ph) 5-257 CF₃ Me NO₂ —CH₂—CO— (4-Me-Ph) 5-258 CF₃ Et NO₂ —CH₂—CO— (4-Me-Ph) 5-259 OMe Me NO₂ —CH₂—CO— (4-Me-Ph) 5-260 OMe Et NO₂ —CH₂—CO— (4-Me-Ph) 5-261 NO₂ Me NO₂ —CH₂—CO— (4-Me-Ph) 5-262 NO₂ Et NO₂ —CH₂—CO— (4-Me-Ph) 5-263 SO₂Me Me NO₂ —CH₂—CO— (4-Me-Ph) 5-264 SO₂Me Et NO₂ —CH₂—CO— (4-Me-Ph) 5-265 CH₂OMe Me NO₂ —CH₂—CO— (4-Me-Ph) 5-266 CH₂OMe Et NO₂ —CH₂—CO— (4-Me-Ph) 5-267 CH₂SO₂Me Me NO₂ —CH₂—CO— (4-Me-Ph) 5-268 CH₂SO₂Me Et NO₂ —CH₂—CO— (4-Me-Ph) 5-269 CH₂OCH₂CH₂OMe Me NO₂ —CH₂—CO— (4-Me-Ph) 5-270 CH₂OCH₂CH₂OMe Et NO₂ —CH₂—CO— (4-Me-Ph)

TABLE 6 Compounds of the formula (I) according to the invention in which R¹ is ethyl and R² is hydrogen.

Physical data: ¹H-NMR: No. X R³ Y R⁴ δ [CDCl₃] 6-1 Cl Me SO₂Me —SO₂-n-Pr 6-2 Cl Et SO₂Me —SO₂-n-Pr 6-3 Me Me SO₂Me —SO₂-n-Pr 6-4 Me Et SO₂Me —SO₂-n-Pr 6-5 CF₃ Me SO₂Me —SO₂-n-Pr 6-6 CF₃ Et SO₂Me —SO₂-n-Pr 6-7 OMe Me SO₂Me —SO₂-n-Pr 6-8 OMe Et SO₂Me —SO₂-n-Pr 6-9 NO₂ Me SO₂Me —SO₂-n-Pr 6-10 NO₂ Et SO₂Me —SO₂-n-Pr 6-11 SO₂Me Me SO₂Me —SO₂-n-Pr 6-12 SO₂Me Et SO₂Me —SO₂-n-Pr 6-13 CH₂OMe Me SO₂Me —SO₂-n-Pr 6-14 CH₂OMe Et SO₂Me —SO₂-n-Pr 6-15 CH₂SO₂Me Me SO₂Me —SO₂-n-Pr 6-16 CH₂SO₂Me Et SO₂Me —SO₂-n-Pr 6-17 CH₂OCH₂CH₂OMe Me SO₂Me —SO₂-n-Pr 6-18 CH₂OCH₂CH₂OMe Et SO₂Me —SO₂-n-Pr 6-19 Cl Me Cl —SO₂-n-Pr 6-20 Cl Et Cl —SO₂-n-Pr 6-21 Me Me Cl —SO₂-n-Pr 6-22 Me Et Cl —SO₂-n-Pr 6-23 CF₃ Me Cl —SO₂-n-Pr 6-24 CF₃ Et Cl —SO₂-n-Pr 6-25 OMe Me Cl —SO₂-n-Pr 6-26 OMe Et Cl —SO₂-n-Pr 6-27 NO₂ Me Cl —SO₂-n-Pr 6-28 NO₂ Et Cl —SO₂-n-Pr 6-29 SO₂Me Me Cl —SO₂-n-Pr 6-30 SO₂Me Et Cl —SO₂-n-Pr 6-31 CH₂OMe Me Cl —SO₂-n-Pr 6-32 CH₂OMe Et Cl —SO₂-n-Pr 6-33 CH₂SO₂Me Me Cl —SO₂-n-Pr 6-34 CH₂SO₂Me Et Cl —SO₂-n-Pr 6-35 CH₂OCH₂CH₂OMe Me Cl —SO₂-n-Pr 6-36 CH₂OCH₂CH₂OMe Et Cl —SO₂-n-Pr 6-37 Cl Me Br —SO₂-n-Pr 6-38 Cl Et Br —SO₂-n-Pr 6-39 Me Me Br —SO₂-n-Pr 6-40 Me Et Br —SO₂-n-Pr 6-41 CF₃ Me Br —SO₂-n-Pr 6-42 CF₃ Et Br —SO₂-n-Pr 6-43 OMe Me Br —SO₂-n-Pr 6-44 OMe Et Br —SO₂-n-Pr 6-45 NO₂ Me Br —SO₂-n-Pr 6-46 NO₂ Et Br —SO₂-n-Pr 6-47 SO₂Me Me Br —SO₂-n-Pr 6-48 SO₂Me Et Br —SO₂-n-Pr 6-49 CH₂OMe Me Br —SO₂-n-Pr 6-50 CH₂OMe Et Br —SO₂-n-Pr 6-51 CH₂SO₂Me Me Br —SO₂-n-Pr 6-52 CH₂SO₂Me Et Br —SO₂-n-Pr 6-53 CH₂OCH₂CH₂OMe Me Br —SO₂-n-Pr 6-54 CH₂OCH₂CH₂OMe Et Br —SO₂-n-Pr 6-55 Cl Me I —SO₂-n-Pr 6-56 Cl Et I —SO₂-n-Pr 6-57 Me Me I —SO₂-n-Pr 6-58 Me Et I —SO₂-n-Pr 6-59 CF₃ Me I —SO₂-n-Pr 6-60 CF₃ Et I —SO₂-n-Pr 6-61 OMe Me I —SO₂-n-Pr 6-62 OMe Et I —SO₂-n-Pr 6-63 NO₂ Me I —SO₂-n-Pr 6-64 NO₂ Et I —SO₂-n-Pr 6-65 SO₂Me Me I —SO₂-n-Pr 6-66 SO₂Me Et I —SO₂-n-Pr 6-67 CH₂OMe Me I —SO₂-n-Pr 6-68 CH₂OMe Et I —SO₂-n-Pr 6-69 CH₂SO₂Me Me I —SO₂-n-Pr 6-70 CH₂SO₂Me Et I —SO₂-n-Pr 6-71 CH₂OCH₂CH₂OMe Me I —SO₂-n-Pr 6-72 CH₂OCH₂CH₂OMe Et I —SO₂-n-Pr 6-73 Cl Me NO₂ —SO₂-n-Pr 6-74 Cl Et NO₂ —SO₂-n-Pr 6-75 Me Me NO₂ —SO₂-n-Pr 6-76 Me Et NO₂ —SO₂-n-Pr 6-77 CF₃ Me NO₂ —SO₂-n-Pr 6-78 CF₃ Et NO₂ —SO₂-n-Pr 6-79 OMe Me NO₂ —SO₂-n-Pr 6-80 OMe Et NO₂ —SO₂-n-Pr 6-81 NO₂ Me NO₂ —SO₂-n-Pr 6-82 NO₂ Et NO₂ —SO₂-n-Pr 6-83 SO₂Me Me NO₂ —SO₂-n-Pr 6-84 SO₂Me Et NO₂ —SO₂-n-Pr 6-85 CH₂OMe Me NO₂ —SO₂-n-Pr 6-86 CH₂OMe Et NO₂ —SO₂-n-Pr 6-87 CH₂SO₂Me Me NO₂ —SO₂-n-Pr 6-88 CH₂SO₂Me Et NO₂ —SO₂-n-Pr 6-89 CH₂OCH₂CH₂OMe Me NO2 —SO₂-n-Pr 6-90 CH₂OCH₂CH₂OMe Et NO₂ —SO₂-n-Pr 6-91 Cl Me SO₂Me —CO-Ph 6-92 Cl Et SO₂Me —CO-Ph 6-93 Me Me SO₂Me —CO-Ph 6-94 Me Et SO₂Me —CO-Ph 6-95 CF₃ Me SO₂Me —CO-Ph 6-96 CF₃ Et SO₂Me —CO-Ph 6-97 OMe Me SO₂Me —CO-Ph 6-98 OMe Et SO₂Me —CO-Ph 6-99 NO₂ Me SO₂Me —CO-Ph 6-100 NO₂ Et SO₂Me —CO-Ph 6-101 SO₂Me Me SO₂Me —CO-Ph 6-102 SO₂Me Et SO₂Me —CO-Ph 6-103 CH₂OMe Me SO₂Me —CO-Ph 6-104 CH₂OMe Et SO₂Me —CO-Ph 6-105 CH₂SO₂Me Me SO₂Me —CO-Ph 6-106 CH₂SO₂Me Et SO₂Me —CO-Ph 6-107 CH₂OCH₂CH₂OMe Me SO₂Me —CO-Ph 6-108 CH₂OCH₂CH₂OMe Et SO₂Me —CO-Ph 6-109 Cl Me Cl —CO-Ph 6-110 Cl Et Cl —CO-Ph 6-111 Me Me Cl —CO-Ph 6-112 Me Et Cl —CO-Ph 6-113 CF₃ Me Cl —CO-Ph 6-114 CF₃ Et Cl —CO-Ph 6-115 OMe Me Cl —CO-Ph 6-116 OMe Et Cl —CO-Ph 6-117 NO₂ Me Cl —CO-Ph 6-118 NO₂ Et Cl —CO-Ph 6-119 SO₂Me Me Cl —CO-Ph 6-120 SO₂Me Et Cl —CO-Ph 6-121 CH₂OMe Me Cl —CO-Ph 6-122 CH₂OMe Et Cl —CO-Ph 6-123 CH₂SO₂Me Me Cl —CO-Ph 6-124 CH₂SO₂Me Et Cl —CO-Ph 6-125 CH₂OCH₂CH₂OMe Me Cl —CO-Ph 6-126 CH₂OCH₂CH₂OMe Et Cl —CO-Ph 6-127 Cl Me Br —CO-Ph 6-128 Cl Et Br —CO-Ph 6-129 Me Me Br —CO-Ph 6-130 Me Et Br —CO-Ph 6-131 CF₃ Me Br —CO-Ph 6-132 CF₃ Et Br —CO-Ph 6-133 OMe Me Br —CO-Ph 6-134 OMe Et Br —CO-Ph 6-135 NO₂ Me Br —CO-Ph 6-136 NO₂ Et Br —CO-Ph 6-137 SO₂Me Me Br —CO-Ph 6-138 SO₂Me Et Br —CO-Ph 6-139 CH₂OMe Me Br —CO-Ph 6-140 CH₂OMe Et Br —CO-Ph 6-141 CH₂SO₂Me Me Br —CO-Ph 6-142 CH₂SO₂Me Et Br —CO-Ph 6-143 CH₂OCH₂CH₂OMe Me Br —CO-Ph 6-144 CH₂OCH₂CH₂OMe Et Br —CO-Ph 6-145 Cl Me I —CO-Ph 6-146 Cl Et I —CO-Ph 6-147 Me Me I —CO-Ph 6-148 Me Et I —CO-Ph 6-149 CF₃ Me I —CO-Ph 6-150 CF₃ Et I —CO-Ph 6-151 OMe Me I —CO-Ph 6-152 OMe Et I —CO-Ph 6-153 NO₂ Me I —CO-Ph 6-154 NO₂ Et I —CO-Ph 6-155 SO₂Me Me I —CO-Ph 6-156 SO₂Me Et I —CO-Ph 6-157 CH₂OMe Me I —CO-Ph 6-158 CH₂OMe Et I —CO-Ph 6-159 CH₂SO₂Me Me I —CO-Ph 6-160 CH₂SO₂Me Et I —CO-Ph 6-161 CH₂OCH₂CH₂OMe Me I —CO-Ph 6-162 CH₂OCH₂CH₂OMe Et I —CO-Ph 6-163 Cl Me NO₂ —CO-Ph 6-164 Cl Et NO₂ —CO-Ph 6-165 Me Me NO₂ —CO-Ph 6-166 Me Et NO₂ —CO-Ph 6-167 CF₃ Me NO₂ —CO-Ph 6-168 CF₃ Et NO₂ —CO-Ph 6-169 OMe Me NO₂ —CO-Ph 6-170 OMe Et NO₂ —CO-Ph 6-171 NO₂ Me NO₂ —CO-Ph 6-172 NO₂ Et NO₂ —CO-Ph 6-173 SO₂Me Me NO₂ —CO-Ph 6-174 SO₂Me Et NO₂ —CO-Ph 6-175 CH₂OMe Me NO₂ —CO-Ph 6-176 CH₂OMe Et NO₂ —CO-Ph 6-177 CH₂SO₂Me Me NO₂ —CO-Ph 6-178 CH₂SO₂Me Et NO₂ —CO-Ph 6-179 CH₂OCH₂CH₂OMe Me NO₂ —CO-Ph 6-180 CH₂OCH₂CH₂OMe Et NO₂ —CO-Ph 6-181 Cl Me SO₂Me —CH₂—CO- (4-Me-Ph) 6-182 Cl Et SO₂Me CH₂—CO- (4-Me-Ph) 6-183 Me Me SO₂Me CH₂—CO- (4-Me-Ph) 6-184 Me Et SO₂Me CH₂—CO- (4-Me-Ph) 6-185 CF₃ Me SO₂Me CH_(2—CO-) (4-Me-Ph) 6-186 CF₃ Et SO₂Me CH₂—CO- (4-Me-Ph) 6-187 OMe Me SO₂Me CH₂—CO- (4-Me-Ph) 6-188 OMe Et SO₂Me CH₂—CO- (4-Me-Ph) 6-189 NO₂ Me SO₂Me CH₂—CO- (4-Me-Ph) 6-190 NO₂ Et SO₂Me —CH₂—CO- (4-Me-Ph) 6-191 SO₂Me Me SO₂Me —CH₂—CO- (4-Me-Ph) 6-192 SO₂Me Et SO₂Me —CH₂—CO- (4-Me-Ph) 6-193 CH₂OMe Me SO₂Me —CH₂—CO- (4-Me-Ph) 6-194 CH₂OMe Et SO₂Me —CH₂—CO- (4-Me-Ph) 6-195 CH₂SO₂Me Me SO₂Me —CH₂—CO- (4-Me-Ph) 6-196 CH₂SO₂Me Et SO₂Me —CH₂—CO- (4-Me-Ph) 6-197 CH₂OCH₂CH₂OMe Me SO₂Me —CH₂—CO- (4-Me-Ph) 6-198 CH₂OCH₂CH₂OMe Et SO₂Me —CH₂—CO- (4-Me-Ph) 6-199 Cl Me Cl —CH₂—CO- (4-Me-Ph) 6-200 Cl Et Cl —CH₂—CO- (4-Me-Ph) 6-201 Me Me Cl —CH₂—CO- (4-Me-Ph) 6-202 Me Et Cl —CH₂—CO- (4-Me-Ph) 6-203 CF₃ Me Cl —CH₂—CO- (4-Me-Ph) 6-204 CF₃ Et Cl —CH₂—CO- (4-Me-Ph) 6-205 OMe Me Cl —CH₂—CO- (4-Me-Ph) 6-206 OMe Et Cl —CH₂—CO- (4-Me-Ph) 6-207 NO₂ Me Cl —CH₂—CO- (4-Me-Ph) 6-208 NO₂ Et Cl —CH₂—CO- (4-Me-Ph) 6-209 SO₂Me Me Cl —CH₂—CO- (4-Me-Ph) 6-210 SO₂Me Et Cl —CH₂—CO- (4-Me-Ph) 6-211 CH₂OMe Me Cl —CH₂—CO- (4-Me-Ph) 6-212 CH₂OMe Et Cl —CH₂—CO- (4-Me-Ph) 6-213 CH₂SO₂Me Me Cl —CH₂—CO- (4-Me-Ph) 6-214 CH₂SO₂Me Et Cl —CH₂—CO- (4-Me-Ph) 6-215 CH₂OCH₂CH₂OMe Me Cl —CH₂—CO- (4-Me-Ph) 6-216 CH₂OCH₂CH₂OMe Et Cl —CH₂—CO- (4-Me-Ph) 6-217 Cl Me Br —CH₂—CO- (4-Me-Ph) 6-218 Cl Et Br —CH₂—CO- (4-Me-Ph) 6-219 Me Me Br —CH₂—CO- (4-Me-Ph) 6-220 Me Et Br —CH₂—CO- (4-Me-Ph) 6-221 CF₃ Me Br —CH₂—CO- (4-Me-Ph) 6-222 CF₃ Et Br —CH₂—CO- (4-Me-Ph) 6-223 OMe Me Br —CH₂—CO- (4-Me-Ph) 6-224 OMe Et Br —CH₂—CO- (4-Me-Ph) 6-225 NO₂ Me Br —CH₂—CO- (4-Me-Ph) 6-226 NO₂ Et Br —CH₂—CO- (4-Me-Ph) 6-227 SO₂Me Me Br —CH₂—CO- (4-Me-Ph) 6-228 SO₂Me Et Br —CH₂—CO- (4-Me-Ph) 6-229 CH₂OMe Me Br —CH₂—CO- (4-Me-Ph) 6-230 CH₂OMe Et Br —CH₂—CO- (4-Me-Ph) 6-231 CH₂SO₂Me Me Br —CH₂—CO- (4-Me-Ph) 6-232 CH₂SO₂Me Et Br —CH₂—CO- (4-Me-Ph) 6-233 CH₂OCH₂CH₂OMe Me Br —CH₂—CO- (4-Me-Ph) 6-234 CH₂OCH₂CH₂OMe Et Br —CH₂—CO- (4-Me-Ph) 6-235 Cl Me I —CH₂—CO- (4-Me-Ph) 6-236 Cl Et I —CH₂—CO- (4-Me-Ph) 6-237 Me Me I —CH₂—CO- (4-Me-Ph) 6-238 Me Et I —CH₂—CO- (4-Me-Ph) 6-239 CF₃ Me I —CH₂—CO- (4-Me-Ph) 6-240 CF₃ Et I —CH₂—CO- (4-Me-Ph) 6-241 OMe Me I —CH₂—CO- (4-Me-Ph) 6-242 OMe Et I —CH₂—CO- (4-Me-Ph) 6-243 NO₂ Me I —CH₂—CO- (4-Me-Ph) 6-244 NO₂ Et I —CH₂—CO- (4-Me-Ph) 6-245 SO₂Me Me I —CH₂—CO- (4-Me-Ph) 6-246 SO₂Me Et I —CH₂—CO- (4-Me-Ph) 6-247 CH₂OMe Me I —CH₂—CO- (4-Me-Ph) 6-248 CH₂OMe Et I —CH₂—CO- (4-Me-Ph) 6-249 CH₂SO₂Me Me I —CH₂—CO- (4-Me-Ph) 6-250 CH₂SO₂Me Et I —CH₂—CO- (4-Me-Ph) 6-251 CH₂OCH₂CH₂OMe Me I —CH₂—CO- (4-Me-Ph) 6-252 CH₂OCH₂CH₂OMe Et I —CH₂—CO- (4-Me-Ph) 6-253 Cl Me NO₂ —CH₂—CO- (4-Me-Ph) 6-254 Cl Et NO₂ —CH₂—CO- (4-Me-Ph) 6-255 Me Me NO₂ —CH₂—CO- (4-Me-Ph) 6-256 Me Et NO₂ —CH₂—CO- (4-Me-Ph) 6-257 CF₃ Me NO₂ —CH₂—CO- (4-Me-Ph) 6-258 CF₃ Et NO₂ —CH₂—CO- (4-Me-Ph) 6-259 OMe Me NO₂ —CH₂—CO- (4-Me-Ph) 6-260 OMe Et NO₂ —CH₂—CO- (4-Me-Ph) 6-261 NO₂ Me NO₂ —CH₂—CO- (4-Me-Ph) 6-262 NO₂ Et NO₂ —CH₂—CO- (4-Me-Ph) 6-263 SO₂Me Me NO₂ —CH₂—CO- (4-Me-Ph) 6-264 SO₂Me Et NO₂ —CH₂—CO- (4-Me-Ph) 6-265 CH₂OMe Me NO₂ —CH₂—CO- (4-Me-Ph) 6-266 CH₂OMe Et NO₂ —CH₂—CO- (4-Me-Ph) 6-267 CH₂SO₂Me Me NO₂ —CH₂—CO- (4-Me-Ph) 6-268 CH₂SO₂Me Et NO₂ —CH₂—CO- (4-Me-Ph) 6-269 CH₂OCH₂CH₂OMe Me NO₂ —CH₂—CO- (4-Me-Ph) 6-270 CH₂OCH₂CH₂OMe Et NO₂ —CH₂—CO- (4-Me-Ph)

TABLE 7 Compounds of the formula (I) according to the invention in which R¹ and R² are each methyl.

Physical data: ¹H-NMR: No. X R³ Y R⁴ δ [CDCl₃] 7-1 Cl Me SO₂Me —SO₂-n-Pr 7-2 Cl Et SO₂Me —SO₂-n-Pr 7-3 Me Me SO₂Me —SO₂-n-Pr 7-4 Me Et SO₂Me —SO₂-n-Pr 7-5 CF₃ Me SO₂Me —SO₂-n-Pr 7-6 CF₃ Et SO₂Me —SO₂-n-Pr 7-7 OMe Me SO₂Me —SO₂-n-Pr 7-8 OMe Et SO₂Me —SO₂-n-Pr 7-9 NO₂ Me SO₂Me —SO₂-n-Pr 7-10 NO₂ Et SO₂Me —SO₂-n-Pr 7-11 SO₂Me Me SO₂Me —SO₂-n-Pr 7-12 SO₂Me Et SO₂Me —SO₂-n-Pr 7-13 CH₂OMe Me SO₂Me —SO₂-n-Pr 7-14 CH₂OMe Et SO₂Me —SO₂-n-Pr 7-15 CH₂SO₂Me Me SO₂Me —SO₂-n-Pr 7-16 CH₂SO₂Me Et SO₂Me —SO₂-n-Pr 7-17 CH₂OCH₂CH₂OMe Me SO₂Me —SO₂-n-Pr 7-18 CH₂OCH₂CH₂OMe Et SO₂Me —SO₂-n-Pr 7-19 Cl Me Cl —SO₂-n-Pr 7-20 Cl Et Cl —SO₂-n-Pr 7-21 Me Me Cl —SO₂-n-Pr 7-22 Me Et Cl —SO₂-n-Pr 7-23 CF₃ Me Cl —SO₂-n-Pr 7-24 CF₃ Et Cl —SO₂-n-Pr 7-25 OMe Me Cl —SO₂-n-Pr 7-26 OMe Et Cl —SO₂-n-Pr 7-27 NO₂ Me Cl —SO₂-n-Pr 7-28 NO₂ Et Cl —SO₂-n-Pr 7-29 SO₂Me Me Cl —SO₂-n-Pr 7-30 SO₂Me Et Cl —SO₂-n-Pr 7-31 CH₂OMe Me Cl —SO₂-n-Pr 7-32 CH₂OMe Et Cl —SO₂-n-Pr 7-33 CH₂SO₂Me Me Cl —SO₂-n-Pr 7-34 CH₂SO₂Me Et Cl —SO₂-n-Pr 7-35 CH₂OCH₂CH₂OMe Me Cl —SO₂-n-Pr 7-36 CH₂OCH₂CH₂OMe Et Cl —SO₂-n-Pr 7-37 Cl Me Br —SO₂-n-Pr 7-38 Cl Et Br —SO₂-n-Pr 7-39 Me Me Br —SO₂-n-Pr 7-40 Me Et Br —SO₂-n-Pr 7-41 CF₃ Me Br —SO₂-n-Pr 7-42 CF₃ Et Br —SO₂-n-Pr 7-43 OMe Me Br —SO₂-n-Pr 7-44 OMe Et Br —SO₂-n-Pr 7-45 NO₂ Me Br —SO₂-n-Pr 7-46 NO₂ Et Br —SO₂-n-Pr 7-47 SO₂Me Me Br —SO₂-n-Pr 7-48 SO₂Me Et Br —SO₂-n-Pr 7-49 CH₂OMe Me Br —SO₂-n-Pr 7-50 CH₂OMe Et Br —SO₂-n-Pr 7-51 CH₂SO₂Me Me Br —SO₂-n-Pr 7-52 CH₂SO₂Me Et Br —SO₂-n-Pr 7-53 CH₂OCH₂CH₂OMe Me Br —SO₂-n-Pr 7-54 CH₂OCH₂CH₂OMe Et Br —SO₂-n-Pr 7-55 Cl Me I —SO₂-n-Pr 7-56 Cl Et I —SO₂-n-Pr 7-57 Me Me I —SO₂-n-Pr 7-58 Me Et I —SO₂-n-Pr 7-59 CF₃ Me I —SO₂-n-Pr 7-60 CF₃ Et I —SO₂-n-Pr 7-61 OMe Me I —SO₂-n-Pr 7-62 OMe Et I —SO₂-n-Pr 7-63 NO₂ Me I —SO₂-n-Pr 7-64 NO₂ Et I —SO₂-n-Pr 7-65 SO₂Me Me I —SO₂-n-Pr 7-66 SO₂Me Et I —SO₂-n-Pr 7-67 CH₂OMe Me I —SO₂-n-Pr 7-68 CH₂OMe Et I —SO₂-n-Pr 7-69 CH₂SO₂Me Me I —SO₂-n-Pr 7-70 CH₂SO₂Me Et I —SO₂-n-Pr 7-71 CH₂OCH₂CH₂OMe Me I —SO₂-n-Pr 7-72 CH₂OCH₂CH₂OMe Et I —SO₂-n-Pr 7-73 Cl Me NO₂ —SO₂-n-Pr 7-74 Cl Et NO₂ —SO₂-n-Pr 7-75 Me Me NO₂ —SO₂-n-Pr 7-76 Me Et NO₂ —SO₂-n-Pr 7-77 CF₃ Me NO₂ —SO₂-n-Pr 7-78 CF₃ Et NO₂ —SO₂-n-Pr 7-79 OMe Me NO₂ —SO₂-n-Pr 7-80 OMe Et NO₂ —SO₂-n-Pr 7-81 NO₂ Me NO₂ —SO₂-n-Pr 7-82 NO₂ Et NO₂ —SO₂-n-Pr 7-83 SO₂Me Me NO₂ —SO₂-n-Pr 7-84 SO₂Me Et NO₂ —SO₂-n-Pr 7-85 CH₂OMe Me NO₂ —SO₂-n-Pr 7-86 CH₂OMe Et NO₂ —SO₂-n-Pr 7-87 CH₂SO₂Me Me NO₂ —SO₂-n-Pr 7-88 CH₂SO₂Me Et NO₂ —SO₂-n-Pr 7-89 CH₂OCH₂CH₂OMe Me NO₂ —SO₂-n-Pr 7-90 CH₂OCH₂CH₂OMe Et NO₂ —SO₂-n-Pr 7-91 Cl Me SO₂Me —CO-Ph 7-92 Cl Et SO₂Me —CO-Ph 7-93 Me Me SO₂Me —CO-Ph 7-94 Me Et SO₂Me —CO-Ph 7-95 CF₃ Me SO₂Me —CO-Ph 7-96 CF₃ Et SO₂Me —CO-Ph 7-97 OMe Me SO₂Me —CO-Ph 7-98 OMe Et SO₂Me —CO-Ph 7-99 NO₂ Me SO₂Me —CO-Ph 7-100 NO₂ Et SO₂Me —CO-Ph 7-101 SO₂Me Me SO₂Me —CO-Ph 7-102 SO₂Me Et SO₂Me —CO-Ph 7-103 CH₂OMe Me SO₂Me —CO-Ph 7-104 CH₂OMe Et SO₂Me —CO-Ph 7-105 CH₂SO₂Me Me SO₂Me —CO-Ph 7-106 CH₂SO₂Me Et SO₂Me —CO-Ph 7-107 CH₂OCH₂CH₂OMe Me SO₂Me —CO-Ph 7-108 CH₂OCH₂CH₂OMe Et SO₂Me —CO-Ph 7-109 Cl Me Cl —CO-Ph 7-110 Cl Et Cl —CO-Ph 7-111 Me Me Cl —CO-Ph 7-112 Me Et Cl —CO-Ph 7-113 CF₃ Me Cl —CO-Ph 7-114 CF₃ Et Cl —CO-Ph 7-115 OMe Me Cl —CO-Ph 7-116 OMe Et Cl —CO-Ph 7-117 NO₂ Me Cl —CO-Ph 7-118 NO₂ Et Cl —CO-Ph 7-119 SO₂Me Me Cl —CO-Ph 7-120 SO₂Me Et Cl —CO-Ph 7-121 CH₂OMe Me Cl —CO-Ph 7-122 CH₂OMe Et Cl —CO-Ph 7-123 CH₂SO₂Me Me Cl —CO-Ph 7-124 CH₂SO₂Me Et Cl —CO-Ph 7-125 CH₂OCH₂CH₂OMe Me Cl —CO-Ph 7-126 CH₂OCH₂CH₂OMe Et Cl —CO-Ph 7-127 Cl Me Br —CO-Ph 7-128 Cl Et Br —CO-Ph 7-129 Me Me Br —CO-Ph 7-130 Me Et Br —CO-Ph 7-131 CF₃ Me Br —CO-Ph 7-132 CF₃ Et Br —CO-Ph 7-133 OMe Me Br —CO-Ph 7-134 OMe Et Br —CO-Ph 7-135 NO₂ Me Br —CO-Ph 7-136 NO₂ Et Br —CO-Ph 7-137 SO₂Me Me Br —CO-Ph 7-138 SO₂Me Et Br —CO-Ph 7-139 CH₂OMe Me Br —CO-Ph 7-140 CH₂OMe Et Br —CO-Ph 7-141 CH₂SO₂Me Me Br —CO-Ph 7-142 CH₂SO₂Me Et Br —CO-Ph 7-143 CH₂OCH₂CH₂OMe Me Br —CO-Ph 7-144 CH₂OCH₂CH₂OMe Et Br —CO-Ph 7-145 Cl Me I —CO-Ph 7-146 Cl Et I —CO-Ph 7-147 Me Me I —CO-Ph 7-148 Me Et I —CO-Ph 7-149 CF₃ Me I —CO-Ph 7-150 CF₃ Et I —CO-Ph 7-151 OMe Me I —CO-Ph 7-152 OMe Et I —CO-Ph 7-153 NO₂ Me I —CO-Ph 7-154 NO₂ Et I —CO-Ph 7-155 SO₂Me Me I —CO-Ph 7-156 SO₂Me Et I —CO-Ph 7-157 CH₂OMe Me I —CO-Ph 7-158 CH₂OMe Et I —CO-Ph 7-159 CH₂SO₂Me Me I —CO-Ph 7-160 CH₂SO₂Me Et I —CO-Ph 7-161 CH₂OCH₂CH₂OMe Me I —CO-Ph 7-162 CH₂OCH₂CH₂OMe Et I —CO-Ph 7-163 Cl Me NO₂ —CO-Ph 7-164 Cl Et NO₂ —CO-Ph 7-165 Me Me NO₂ —CO-Ph 7-166 Me Et NO₂ —CO-Ph 7-167 CF₃ Me NO₂ —CO-Ph 7-168 CF₃ Et NO₂ —CO-Ph 7-169 OMe Me NO₂ —CO-Ph 7-170 OMe Et NO₂ —CO-Ph 7-171 NO₂ Me NO₂ —CO-Ph 7-172 NO₂ Et NO₂ —CO-Ph 7-173 SO₂Me Me NO₂ —CO-Ph 7-174 SO₂Me Et NO₂ —CO-Ph 7-175 CH₂OMe Me NO₂ —CO-Ph 7-176 CH₂OMe Et NO₂ —CO-Ph 7-177 CH₂SO₂Me Me NO₂ —CO-Ph 7-178 CH₂SO₂Me Et NO₂ —CO-Ph 7-179 CH₂OCH₂CH₂OMe Me NO₂ —CO-Ph 7-180 CH₂OCH₂CH₂OMe Et NO₂ —CO-Ph 7-181 Cl Me SO₂Me —CH₂—CO- (4-Me-Ph) 7-182 Cl Et SO₂Me —CH₂—CO- (4-Me-Ph) 7-183 Me Me SO₂Me —CH₂—CO- (4-Me-Ph) 7-184 Me Et SO₂Me —CH₂—CO- (4-Me-Ph) 7-185 CF₃ Me SO₂Me —CH₂—CO- (4-Me-Ph) 7-186 CF₃ Et SO₂Me —CH₂—CO- (4-Me-Ph) 7-187 OMe Me SO₂Me —CH₂—CO- (4-Me-Ph) 7-188 OMe Et SO₂Me —CH₂—CO- (4-Me-Ph) 7-189 NO₂ Me SO₂Me —CH₂—CO- (4-Me-Ph) 7-190 NO₂ Et SO₂Me —CH₂—CO- (4-Me-Ph) 7-191 SO₂Me Me SO₂Me —CH₂—CO- (4-Me-Ph) 7-192 SO₂Me Et SO₂Me —CH₂—CO- (4-Me-Ph) 7-193 CH₂OMe Me SO₂Me —CH₂—CO- (4-Me-Ph) 7-194 CH₂OMe Et SO₂Me —CH₂—CO- (4-Me-Ph) 7-195 CH₂SO₂Me Me SO₂Me —CH₂—CO- (4-Me-Ph) 7-196 CH₂SO₂Me Et SO₂Me —CH₂—CO- (4-Me-Ph) 7-197 CH₂OCH₂CH₂OMe Me SO₂Me —CH₂—CO- (4-Me-Ph) 7-198 CH₂OCH₂CH₂OMe Et SO₂Me —CH₂—CO- (4-Me-Ph) 7-199 Cl Me Cl —CH₂—CO- (4-Me-Ph) 7-200 Cl Et Cl —CH₂—CO- (4-Me-Ph) 7-201 Me Me Cl —CH₂—CO- (4-Me-Ph) 7-202 Me Et Cl —CH₂—CO- (4-Me-Ph) 7-203 CF₃ Me Cl —CH₂—CO- (4-Me-Ph) 7-204 CF₃ Et Cl —CH₂—CO- (4-Me-Ph) 7-205 OMe Me Cl —CH₂—CO- (4-Me-Ph) 7-206 OMe Et Cl —CH₂—CO- (4-Me-Ph) 7-207 NO₂ Me Cl —CH₂—CO- (4-Me-Ph) 7-208 NO₂ Et Cl —CH₂—CO- (4-Me-Ph) 7-209 SO₂Me Me Cl —CH₂—CO- (4-Me-Ph) 7-210 SO₂Me Et Cl —CH₂—CO- (4-Me-Ph) 7-211 CH₂OMe Me Cl —CH₂—CO- (4-Me-Ph) 7-212 CH₂OMe Et Cl —CH₂—CO- (4-Me-Ph) 7-213 CH₂SO₂Me Me Cl —CH₂—CO- (4-Me-Ph) 7-214 CH₂SO₂Me Et Cl —CH₂—CO- (4-Me-Ph) 7-215 CH₂OCH₂CH₂OMe Me Cl —CH₂—CO- (4-Me-Ph) 7-216 CH₂OCH₂CH₂OMe Et Cl —CH₂—CO- (4-Me-Ph) 7-217 Cl Me Br —CH₂—CO- (4-Me-Ph) 7-218 Cl Et Br —CH₂—CO- (4-Me-Ph) 7-219 Me Me Br —CH₂—CO- (4-Me-Ph) 7-220 Me Et Br —CH₂—CO- (4-Me-Ph) 7-221 CF₃ Me Br —CH₂—CO- (4-Me-Ph) 7-222 CF₃ Et Br —CH₂—CO- (4-Me-Ph) 7-223 OMe Me Br —CH₂—CO- (4-Me-Ph) 7-224 OMe Et Br —CH₂—CO- (4-Me-Ph) 7-225 NO₂ Me Br —CH₂—CO- (4-Me-Ph) 7-226 NO₂ Et Br —CH₂—CO- (4-Me-Ph) 7-227 SO₂Me Me Br —CH₂—CO- (4-Me-Ph) 7-228 SO₂Me Et Br —CH₂—CO- (4-Me-Ph) 7-229 CH₂OMe Me Br —CH₂—CO- (4-Me-Ph) 7-230 CH₂OMe Et Br —CH₂—CO- (4-Me-Ph) 7-231 CH₂SO₂Me Me Br —CH₂—CO- (4-Me-Ph) 7-232 CH₂SO₂Me Et Br —CH₂—CO- (4-Me-Ph) 7-233 CH₂OCH₂CH₂OMe Me Br —CH₂—CO- (4-Me-Ph) 7-234 CH₂OCH₂CH₂OMe Et Br —CH₂—CO- (4-Me-Ph) 7-235 Cl Me I —CH₂—CO- (4-Me-Ph) 7-236 Cl Et I —CH₂—CO- (4-Me-Ph) 7-237 Me Me I —CH₂—CO- (4-Me-Ph) 7-238 Me Et I —CH₂—CO- (4-Me-Ph) 7-239 CF₃ Me I —CH₂—CO- (4-Me-Ph) 7-240 CF₃ Et I —CH₂—CO- (4-Me-Ph) 7-241 OMe Me I —CH₂—CO- (4-Me-Ph) 7-242 OMe Et I —CH₂—CO- (4-Me-Ph) 7-243 NO₂ Me I —CH₂—CO- (4-Me-Ph) 7-244 NO₂ Et I —CH₂—CO- (4-Me-Ph) 7-245 SO₂Me Me I —CH₂—CO- (4-Me-Ph) 7-246 SO₂Me Et I —CH₂—CO- (4-Me-Ph) 7-247 CH₂OMe Me I —CH₂—CO- (4-Me-Ph) 7-248 CH₂OMe Et I —CH₂—CO- (4-Me-Ph) 7-249 CH₂SO₂Me Me I —CH₂—CO- (4-Me-Ph) 7-250 CH₂SO₂Me Et I —CH₂—CO- (4-Me-Ph) 7-251 CH₂OCH₂CH₂OMe Me I —CH₂—CO- (4-Me-Ph) 7-252 CH₂OCH₂CH₂OMe Et I —CH₂—CO- (4-Me-Ph) 7-253 Cl Me NO₂ —CH₂—CO- (4-Me-Ph) 7-254 Cl Et NO₂ —CH₂—CO- (4-Me-Ph) 7-255 Me Me NO₂ —CH₂—CO- (4-Me-Ph) 7-256 Me Et NO₂ —CH₂—CO- (4-Me-Ph) 7-257 CF₃ Me NO₂ —CH₂—CO- (4-Me-Ph) 7-258 CF₃ Et NO₂ —CH₂—CO- (4-Me-Ph) 7-259 OMe Me NO₂ —CH₂—CO- (4-Me-Ph) 7-260 OMe Et NO₂ —CH₂—CO- (4-Me-Ph) 7-261 NO₂ Me NO₂ —CH₂—CO- (4-Me-Ph) 7-262 NO₂ Et NO₂ —CH₂—CO- (4-Me-Ph) 7-263 SO₂Me Me NO₂ —CH₂—CO- (4-Me-Ph) 7-264 SO₂Me Et NO₂ —CH₂—CO- (4-Me-Ph) 7-265 CH₂OMe Me NO₂ —CH₂—CO- (4-Me-Ph) 7-266 CH₂OMe Et NO₂ —CH₂—CO- (4-Me-Ph) 7-267 CH₂SO₂Me Me NO₂ —CH₂—CO- (4-Me-Ph) 7-268 CH₂SO₂Me Et NO₂ —CH₂—CO- (4-Me-Ph) 7-269 CH₂OCH₂CH₂OMe Me NO₂ —CH₂—CO- (4-Me-Ph) 7-270 CH₂OCH₂CH₂OMe Et NO₂ —CH₂—CO- (4-Me-Ph)

B. FORMULATION EXAMPLES

-   a) A dust is obtained by mixing 10 parts by weight of a compound of     the formula (I) and/or its salts and 90 parts by weight of talc as     inert substance and comminuting the mixture in a hammer mill. -   b) A wettable powder which is readily dispersible in water is     obtained by mixing 25 parts by weight of a compound of the     formula (I) and/or its salts, 64 parts by weight of     kaolin-containing quartz as inert substance, 10 parts by weight of     potassium lignosulfonate and 1 part by weight of sodium     oleoylmethyltaurinate as wetter and dispersant, and grinding the     mixture in a pinned-disk mill. -   c) A dispersion concentrate which is readily dispersible in water is     obtained by mixing 20 parts by weight of a compound of the     formula (I) and/or its salts with 6 parts by weight of alkylphenol     polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol     polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral     oil (boiling range for example approximately 255 up to over 277° C.)     and grinding the mixture in a bowl mill to a fineness of below 5     microns. -   d) An emulsifiable concentrate is obtained from 15 parts by weight     of a compound of the formula (I) and/or its salts, 75 parts by     weight of cyclohexanone as solvent and 10 parts by weight of     oxyethylated nonylphenol as emulsifier. -   e) Water-dispersible granules are obtained by mixing     -   75 parts by weight of a compound of the formula (I) and/or its         salts,     -   10 parts by weight of calcium lignosulfonate,     -   5 parts by weight of sodium lauryl sulfate,     -   3 parts by weight of polyvinyl alcohol and     -   7 parts by weight of kaolin,     -   grinding the mixture in a pinned-disk mill and granulating the         powder in a fluidized bed by spraying on water as granulation         liquid. -   f) Water-dispersible granules are also obtained by homogenizing and     precomminuting, in a colloid mill,     -   25 parts by weight of a compound of the formula (I) and/or its         salts,     -   5 parts by weight of sodium         2,2′-dinaphthylmethane-6,6′-disulfonate,     -   2 parts by weight of sodium oleoylmethyltaurinate,     -   1 part by weight of polyvinyl alcohol,     -   17 parts by weight of calcium carbonate and     -   50 parts by weight of water,     -   subsequently grinding the mixture in a bead mill, and atomizing         and drying the resulting suspension in a spray tower by means of         a single-substance nozzle.

C. BIOLOGICAL EXAMPLES

-   1. Herbicidal Pre-Emergence Effect Against Harmful Plants

Seeds of monocotyledonous or dicotyledonous weeds or crop plants are placed in sandy loam soil in wood-fiber pots and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then applied to the surface of the soil cover in the form of an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted), with addition of 0.2% wetter. After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. The damage to the test plants is scored visually in comparison with untreated controls after an experimental time of 3 weeks has elapsed (herbicidal activity in percent (%): 100% activity=plants have died, 0% activity=like control plants). Here, for example the compounds Nos. 1-2, 2-9, 2-10, 2-11 and 3-238 show, at an application rate of 80 g/ha, each at least 90% strength activity against Amaranthus retroflexus and Veronica Persica.

The compounds Nos. 1-237, 1-238, 2-9, 2-10, 2-237 and 2-238 show, at an application rate of 80 g/ha, each at least 90% strength activity against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus galli. The compounds Nos. 1-10, 2-9 and 2-238 show, at an application rate of 80 g/ha, each at least 90% strength activity against Abutilon theophrasti and Matricaria inodora.

-   2. Herbicidal Post-Emergence Activity Against Harmful Plants

Seeds of monocotyledonous or dicotyledonous weeds or crop plants are placed in sandy loam soil in wood-fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the one-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then sprayed onto the green plant parts in the form of an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted), with addition of 0.2% wetter. After the test plants have been left to stand under optimal growth conditions in the greenhouse for approximately 3 weeks, the activity of the preparations is scored visually in comparison with untreated controls (herbicidal activity in percent (%): 100% activity=plants have died, 0% activity=like control plants).

Here, for example the compounds Nos. 1-10, 1-237 and 2-9 show, at an application rate of 80 g/ha, each at least 90% strength activity against Stellaria media and Veronica Persica. The compounds Nos. 1-238, 2-10 and 2-238 show, at an application rate of 80 g/ha, each at least 90% strength activity against Setaria viridis and Viola tricolor. The compounds Nos. 1-2, 1-237, 1-238 and 2-11 show, at an application rate of 80 g/ha, each at least 90% strength activity against Abutilon theophrasti and Echinochloa crus galli. 

The invention claimed is:
 1. A 4-(3-alkylsulfinylbenzoyl)pyrazole of the formula (I) or a salt thereof

in which R¹ is (C₁-C₄)-alkyl, R² is hydrogen or (C₁-C₄)-alkyl, R³ is (C₁-C₆)-alkyl, R⁴ is hydrogen, (C₁-C₆)-alkylsulfonyl, (C₁-C₄)-alkoxy -(C₁-C₆)-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl or benzyl, each of which is substituted by m identical or different radicals from the group consisting of halogen, (C₁-C₄)-alkyl and (C₁-C₄)-alkoxy, X is hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, OR⁵, OCOR⁵, OSO₂R⁵, S(O)_(n)R⁵, SO₂OR⁵, SO₂N(R⁵)₂, NR⁵SO₂R⁵, NR⁵COR⁵, (C₁-C₆)-alkyl-S(O)_(n)R⁵, (C₁-C₆)-alkyl-OR⁵, (C₁-C₆)-alkyl-OCOR⁵, (C₁-C₆)-alkyl-OSO2R⁵, (C₁-C₆) -alkyl-SO₂OR⁵, (C₁-C₆)-alkyl-SO₂N(R⁵)₂or (C₁-C₆)-alkyl-NR⁵COR⁵; Y is fluorine, chlorine, bromine, iodine, nitro or the group SO₂R⁷, R⁵ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, phenyl or phenyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals are substituted by s radicals from the group consisting of hydroxy, mercapto, amino, cyano, nitro, thiocyanato, OR⁶, SR⁶, N(R⁶)₂, NOR⁶, OCOR⁶, SCOR⁶, NR⁶COR⁶, CO₂R⁶, COSR⁶, CON(R⁶)₂, (C₁)-C₄-alkyliminooxy, (C₁-C₄) -alkylcarbonyl, (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl and (C₁-C₄) -alkylsulfonyl; R⁶ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, R⁷ is (C₁-C₄)-alkyl, m is 0, 1, 2, 3, 4 or 5, n is 0, 1 or 2, s is 0, 1, 2 or
 3. 2. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which R¹ is methyl, ethyl, n-propyl or isopropyl, R² is hydrogen, methyl, ethyl, n-propyl or isopropyl, R³ is (C₁-C₄)-alkyl, R⁴ is hydrogen, (C₁-C₃)-alkylsulfonyl, (C₁-C₂)-alkoxy -(C₁-C₄)-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl or benzyl, each of which is substituted by m methyl groups, X is nitro, halogen, (C₁-C₄)-alkyl, trifluoromethyl, (C₁-C₄) -alkoxy, methylsulfonyl, methoxymethyl, methoxymethoxymethyl, ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl, methoxypropoxymethyl, methylsulfonylmethyl, methylsulfonylethoxymethyl, methoxyethylsulfonylmethyl, methylsulfonylethylsulfonylmethyl, Y is fluorine, chlorine, bromine, iodine or the group SO₂R⁷, R⁷ is methyl, ethyl, n-propyl or isopropyl, m is 0, 1, 2 or
 3. 3. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which R¹ is methyl or ethyl, R² is hydrogen, methyl or ethyl, R³ is methyl, ethyl, n-propyl or isopropyl, R⁴ is hydrogen, X is nitro, halogen, (C₁-C₄)-alkyl, trifluoromethyl, (C₁-C₄) -alkoxy, methylsulfonyl, methoxymethyl, methoxymethoxymethyl, ethoxyethoxymethyl, ethoxymethoxymethyl, methoxyethoxymethyl, methoxypropoxymethyl, methylsulfonylmethyl, methylsulfonylethoxymethyl, methoxyethylsulfonylmethyl, methylsulfonylethylsulfonylmethyl, Y is fluorine, chlorine, bromine, iodine or the group SO₂R⁷, R⁷ is methyl or ethyl.
 4. A herbicidal composition which comprises a herbicidally active amount of at least one compound of the formula (I) as claimed in claim
 1. 5. The herbicidal composition as claimed in claim 4 in a mixture with formulation auxiliaries.
 6. A method of controlling unwanted plants, which comprises applying an effective amount of at least one compound of the formula (I) as claimed in claim 1 to plants and/or to a location of unwanted plant growth.
 7. A compound of the formula (I) as claimed in claim 1 capable of controlling unwanted plants.
 8. A method for using a compound as claimed in claim 7, wherein a compound of the formula (I) is employed for controlling unwanted plants in crops of useful plants.
 9. A method as claimed in claim 8, wherein the useful plants are transgenic useful plants.
 10. A method for making a herbicidically active 4-(3-alkylsulfinylbenzol) pyrazole as claimed in claim 1 comprising reacting a compound of formula (II),

with a pyrazole, in which R³ is (C₁-C₆)-alkyl X is hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆) cycloalkyl, OR⁵, OCOR⁵, OSO₂R⁵,S(O)_(n)R⁵, SO₂OR⁵,SO₂ N(R⁵)₂,NR⁵SO₂R⁵, NR⁵COR⁵, (C₁-C₆)-alkyl-S(O)_(n)R⁵, (C₁-C₆)-alkyl-OR⁵, (C₁-C₆)-alkyl-OCOR⁵, (C₁-C₆)-alkyl-OSO2R⁵, (C₁-C6) -alkyl-SO₂OR⁵, (C₁-C₆)-alkyl-SO₂N(R⁵)₂ or (C₁-C₆)-alkyl-NR⁵COR⁵; Y is fluorine, chlorine, bromine, iodine, nitro or the group SO₂R⁷.
 11. A compound of formula (Ia) or a salt thereof


12. A herbicidal composition, comprising a herbicidally active amount of at least one compound of formula (Ia) or salt as claimed in claim
 11. 13. The herbicidal composition as claimed in claim 12 in a mixture with formulation auxillaries.
 14. A method of controlling undesired plants, comprising applying an effective amount of at least one compound of the formula (Ia) as claimed in claim 11 to plants and/or to a location of unwanted plant growth.
 15. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which R^(l) is methyl or ethyl, R² is hydrogen, R³ is methyl, ethyl, n-propyl or isopropyl, R⁴ is hydrogen, X is methyl, chlorine, or methoxymethyl, Y is chlorine, bromine, or the group SO₂R⁷, R⁷ is methyl.
 16. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which R² is (C₁-C₄)-alkyl.
 17. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which R⁴ is (C₁-C₆)-alkylsulfonyl, (C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, or is phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl or benzyl, each of which is substituted by m identical or different radicals from the group consisting of halogen, (C₁-C₄) -alkyl and (C₁-C₄)-alkoxy.
 18. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which X is hydrogen, mercapto, nitro, fluorine, bromine, iodine, cyano, thiocyanato, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-haloalkynyl, (C₃-C₆)-cycloalkyl, OR⁵, OCOR⁵, OSO₂R⁵, S(O)_(n)R⁵, SO₂OR⁵, SO₂N(R⁵)₂, NR⁵SO₂R⁵, NR⁵COR⁵, (C₁-C₆)-alkyl -S(O)_(n)R⁵, (C₁-C₆)-alkyl-OR⁵, (C₁-C₆)-alkyl -OCOR⁵, (C₁-C₆)-alkyl-OSO2R⁵, (C₁-C₆)-alkyl -SO₂OR⁵, (C₁-C₆)-alkyl-SO₂N(R⁵)₂ or (C₁-C₆)-alkyl-NR⁵COR⁵.
 19. The 4-(3-alkylsulfinylbenzoyl)pyrazole as claimed in claim 1 in which Y is fluorine, chlorine, bromine, iodine, or nitro. 